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N-demethylation

N-demethylation

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S-1

Supplementary Material (ESI) for Organic & Biomolecular Chemistry

Further Investigations into the N-Demethylation of Oripavine using Zero-valent Iron as a Redox Catalyst.

Gaik B. Kok and Peter J. Scammells*

Medicinal Chemistry and Drug Action, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville, Victoria, 3052, Australia. E-
mail: peter.scammells@monash.edu; Fax: (+61) 3 9903 9582

General Experimental S-2
Synthesis of Oripavine-N-oxide S-2
General N-Demethylation Procedure S-2
Figure 1 Oripavine-N-oxide Hydrochloride (6)
1
H NMR spectrum in D
2
O S-3
Figure 1A Oripavine-N-oxide Hydrochloride (6)
1
H NMR spectrum in D
2
O (Expansion) S-4
Figure 1B Oripavine-N-oxide Hydrochloride (6)
1
H NMR spectrum in D
2
O (Expansion) S-5
Figure 2 N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O S-6
Figure 2A N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O (Expansion) S-7
Figure 2B N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O (Expansion) S-8
Figure 3 N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O+TFA S-9
Figure 3A N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O+TFA (Expansion) S-10
Figure 3B N-Nororipavine (7) Hydrochloride
1
H NMR spectrum in D
2
O+TFA (Expansion) S-11
Figure 4 N-Nororipavine (7) Hydrochloride
13
C NMR spectrum in D
2
O+TFA S-12
Figure 4A N-Nororipavine (7) Hydrochloride
13
C NMR spectrum in D
2
O+TFA (Expansion) S-13
Figure 4B N-Nororipavine (7) Hydrochloride
13
C NMR spectrum in D
2
O+TFA (Expansion) S-14
Figure 5 N-Nororipavine (7) Hydrochloride High Resolution MS S-15
Table A Specifications for Iron Catalysts used S-16
Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-2


General Experimental
Stainless steel powders 303-L and 316-L were purchased from Alfa Aesar. Iron powder was from Höganäs Sweden. m-CPBA was purchased from Sigma-Aldrich.
All reactions were conducted under an atmosphere of nitrogen. Chloroform and 2-propanol (Merck) were used as supplied. Both solvents were degassed before use:
sonicated for 10 minutes under vacuum and then back-filled with nitrogen. Reactions were monitored using thin layer chromatography (TLC) with pre-coated Merck
5554 Kieselgel 60F
254
aluminum plates using CHCl
3
/MeOH/NH
4
OH (170:30:1) as the mobile phase. The spots were visualized using both UV light and molybdate
stain.
1
H and
13
C NMR were recorded at 400 and 100 MHz, respectively. Chemical shifts (δ ppm) were referenced using solvent residual peaks.

Synthesis of Oripavine-N-oxide hydrochloride (6)
To a stirred solution of oripavine (1.92 g, 6.47 mmol) in CHCl
3
(200 mL) and MeOH (1 mL) at -20
o
C was added m-CPBA (1.54 g of a max 77% reagent)
portionwise over 10 min. The solution was then left to stir for a further 20 minutes. Ice-cold H
2
O (100 mL) was added; the pH of the aqueous phase was adjusted to
2–3 via the addition of 10% HCl. The layers were separated; the aqueous phase was extracted with CHCl
3
(20 mL x 2), saturated with NaCl, and extracted with
CHCl
3
/2-propanol (3:1, 50 mL x 4). The CHCl
3
/2-propanol (3:1) extracts were combined, dried (Na
2
SO
4
), filtered and concentrated to give 6 as an off-white solid,
2.43 g.
1
H NMR of the solid was consistent with the desired product 6 with approximately 0.5 molar equivalent of 2-propanol. This material was used in the
subsequent step without further purification.
1
H NMR (D
2
O) δ 6.80–6.70 (m, 2H), 6.08, 5.98 (each d, J = 6.7 Hz, 1H), 5.56, 5.55 (each s, 1H), 5.32, 5.29 (each d, J
= 6.7 Hz, 1H), 4.79–4.74 (m, 1H), 3.85–3.57 (m, 9H), 3.33, 3.18 (each dd, J = 7.2, 1H), 2.70–2.47 (m, 1H), 2.18–1.98 (m, 1H).

General Procedure for N-Demethylation
To a mixture of oripavine-N-oxide hydrochloride (100 mg, 0.263 mmol) and iron powder (varying amounts; see Tables 1 and 2) was added solvent (10 mL). The
reaction mixture was then stirred at the specified temperature until complete consumption of 6 (via TLC analysis). The mixture was concentrated to dryness and the
remaining residue was subjected to column chromatography on silica gel. Elution with a gradient of CHCl
3
/MeOH (24:1−17:3) gave oripavine followed by N-
nororipavine, both as the corresponding hydrochloride.

The above procedure was repeated substituting iron powder with stainless steel powder 303-L or 316-L (see Table 3).

N-Nororipavine Hydrochloride (7·HCl): Off-white solid, mp >200
o
C dec; [α]
D
24
-188 (c 1.0, 10% HOAc); [lit.
1
[α]
D
24
-194 (c 0.83, 10% HOAc)];


1
H NMR (D
2
O)
δ 6.79–6.73 (m, 2H), 5.90 (d, J = 6.6 Hz, 1H), 5.50 (s, 1H), 5.25 (d, J = 6.6 Hz, 1H), 4.60 (d, J = 6.0, 1H), 3.64 (s, 3 H), 3.46–3.22 (m, 4H), 2.31 (ddd, J = 6.0, 13.3
and 13.3 Hz, 1H), 2.08–2.01 (m, 1H);
13
C NMR (D
2
O/CF
3
CO
2
D) δ 153.0, 142.8, 138.6, 132.0, 124.4, 124.2, 120.8, 117.3, 117.0, 96.1, 87.7, 55.1, 53.2, 44.6, 37.0,
33.5, 33.1; MS (ESI) m/z 284 [M+H]
+
; HRMS C
17
H
18
NO
3
calcd for [M+H]
+
284.1281, found 284.1287.

Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-3


Figure 1.
1
H NMR of Oripavine-N-oxide Hydrochloride (6) in D
2
O
Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-4

0
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-5


Figure 1A.
1
H NMR of Oripavine-N-oxide Hydrochloride (6) in D
2
O (Expansion)

8
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-6


Figure 1B.
1
H NMR of Oripavine-N-oxide Hydrochloride (6) in D
2
O (Expansion)

0
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-7


Figure 2.
1
H NMR of N-Nororipavine (6) Hydrochloride in D
2
O
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-8


Figure 2A.
1
H NMR of N-Nororipavine (7) Hydrochloride in D
2
O (Expansion)

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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-9


Figure 2B.
1
H NMR of N-Nororipavine (7) Hydrochloride in D
2
O (Expansion)
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-10


Figure 3.
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H NMR of N-Nororipavine (7) Hydrochloride in D
2
O +TFA
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-11


Figure 3A.
1
H NMR of N-Nororipavine (7) Hydrochloride in D
2
O +TFA (Expansion)

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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-12


Figure 3B.
1
H NMR of N-Nororipavine (7) Hydrochloride in D
2
O +TFA (Expansion)

1
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PPM 6.80 6.70 6.60 6.50 6.40 6.30 6.20 6.10 6.00 5.90 5.80 5.70 5.60 5.50 5.40 5.30 5.20 5.10 5.00
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-13


Figure 4.
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C NMR of N-Nororipavine (7) Hydrochloride in D
2
O + TFA
PPM 180 160 140 120 100 80 60 40 20 0
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0
4

Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-14


Figure 4A.
13
C NMR of N-Nororipavine (7) Hydrochloride in D
2
O + TFA (Expansion)
PPM 84 80 76 72 68 64 60 56 52 48 44 40 36 32 28
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-15


Figure 4B.
13
C NMR of N-Nororipavine (7) Hydrochloride in D
2
O + TFA (Expansion)

PPM 152 148 144 140 136 132 128 124 120 116 112 108 104 100 96
1
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0
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Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-16


Figure 5. High Resolution MS of N-Nororipavine (7)


Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011
S-17


Table A. Specifications for Iron and Stainless Steel Catalysts

Chemical analysis (%) Catalyst Supplier Physical
properties
Fe Cr Ni Mo Mn Si Other
Iron(0) Höganäs
Sweden
Powder, +212 to
-45 microns
99 0.002 0.01 <5 ppm 0.04
(MnO)
0.13
(SiO
2
)
Bal
303-L Alfa Aesar Powder, -140
mesh
70 17 13
316-L Alfa Aesar Powder, -100
mesh
67.5 17 13 2.5

Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2011

47 (m. 1H).1287. 96.47 mmol) in CHCl3 (200 mL) and MeOH (1 mL) at -20 oC was added m-CPBA (1. 55.80–6. N-Nororipavine Hydrochloride (7·HCl): Off-white solid. MS (ESI) m/z 284 [M+H]+.3 and 13. filtered and concentrated to give 6 as an off-white solid.98 (m. 5. 2.1281.56.43 g.29 (each d.0.0.3 Hz. and extracted with CHCl3/2-propanol (3:1. 2.01 (m.6. 5.2. S-2 .31 (ddd.79–4. 132. m-CPBA was purchased from Sigma-Aldrich. 33. The CHCl3/2-propanol (3:1) extracts were combined. 138. 1H).0. 10% HOAc)]. The mixture was concentrated to dryness and the remaining residue was subjected to column chromatography on silica gel. 124. 1H). 1H NMR (D2O) δ 6.8.5 molar equivalent of 2-propanol.0. 1H). Chemical shifts (δ ppm) were referenced using solvent residual peaks.08–2.1. This material was used in the subsequent step without further purification. 4H). Elution with a gradient of CHCl3/MeOH (24:1−17:3) gave oripavine followed by Nnororipavine. Both solvents were degassed before use: sonicated for 10 minutes under vacuum and then back-filled with nitrogen.0. 1H NMR (D2O) δ 6.1. 5.2. J = 6. All reactions were conducted under an atmosphere of nitrogen. 124.0.1.32.25 (d. 1H).57 (m.8. General Procedure for N-Demethylation To a mixture of oripavine-N-oxide hydrochloride (100 mg. 4. 5.22 (m. 142. 50 mL x 4). 3. 6.08.5.70–2.83. 13C NMR (D2O/CF3CO2D) δ 153.33. 2. 9H). The solution was then left to stir for a further 20 minutes.92 g.4.Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2011 General Experimental Stainless steel powders 303-L and 316-L were purchased from Alfa Aesar. 2H).64 (s.70 (m. [α]D24 -188 (c 1. 1H).79–6. 1H). 44.55 (each s. the aqueous phase was extracted with CHCl3 (20 mL x 2). dried (Na2SO4). saturated with NaCl. found 284. J = 6. J = 6. 87. The spots were visualized using both UV light and molybdate stain. 3.73 (m. 2. see Tables 1 and 2) was added solvent (10 mL).2. The layers were separated. Ice-cold H2O (100 mL) was added. The above procedure was repeated substituting iron powder with stainless steel powder 303-L or 316-L (see Table 3).98 (each d. mp >200 oC dec. The reaction mixture was then stirred at the specified temperature until complete consumption of 6 (via TLC analysis). [lit. J = 6. 6.50 (s.46–3.1 [α]D24 -194 (c 0. 13. 1H).18 (each dd. 1H). 4. Iron powder was from Höganäs Sweden. HRMS C17H18NO3 calcd for [M+H]+ 284. J = 7. both as the corresponding hydrochloride.74 (m.90 (d.18–1. 1H and 13C NMR were recorded at 400 and 100 MHz. 1H NMR of the solid was consistent with the desired product 6 with approximately 0. 5. 1H). J = 6. 53. 3. 33. 10% HOAc). J = 6. Synthesis of Oripavine-N-oxide hydrochloride (6) To a stirred solution of oripavine (1. 1H).7 Hz.6. 0.6 Hz.3.0.85–3. Chloroform and 2-propanol (Merck) were used as supplied. 117. 37.54 g of a max 77% reagent) portionwise over 10 min. 117.7 Hz. 1H). 3 H).6 Hz. respectively. Reactions were monitored using thin layer chromatography (TLC) with pre-coated Merck 5554 Kieselgel 60F254 aluminum plates using CHCl3/MeOH/NH4OH (170:30:1) as the mobile phase. 5. 3.60 (d.7. 1H). 2H). the pH of the aqueous phase was adjusted to 2–3 via the addition of 10% HCl. 3.263 mmol) and iron powder (varying amounts. 120. 5. 2. 5.

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