Reaction & Reagent Summary #1

R''NH2 R'R''NH
R C R' R C R' R OTos R NR'R''
R'' = H or R'' = H or
N carbon chain O carbon chain
R''

CrO3 / H+ or R'R''NH
1. LiAlH4 1. LiAlH4 TosCl / X R',R'' = H or
2. H+ / H2O Cr2O72- / H+ or 2. H+ / H2O pyridine carbon chain
CrO3 / pyridine

OH
R CH R' R CH R' R OH R X
NHR'' OH

Mg /
dry ether
1. R'CHO
R'O CN
2. H+ / H2O
1. R' C R''
R'
O
R C R'' R MgX R O R' R CN
2. H+ / H2O
OH
H+ / H2O
1. CH2O
2. H+ / H2O 1. CO2
2. H+ / H2O
R C OR'

R CH2NHR' R CH2OH CrO3 / H+ or O

R'OH /
Cr2O72- / H+
H+ H+/ R'OH
1. LiAlH4 H2O
1. LiAlH4
CrO3 / pyridine 2. H+ / H2O R C OH SOCl2 R C Cl
2. H+ / H2O
O O

R'R''NH R',R'' = H or
R'NH2
R C H R C H CrO3 / H+ or H+/ carbon chain

N R' = H or O Cr2O72- / H+ H2O

R' R C NR'R''
carbon chain
O