Reaction #166085

Reaction equation

NaCNBH3

Trans-5-amino-2-diphenylmethyl-tetrahydropyran

Cis-(6-benzhydryl-tetrahydropyran-3-yl)-amine

4-nitrobenzaldehyde

acetic acid

→

compound 16d

Yield 80.0%

Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amine

Yield 80.0%

Solvents

methanol

1,2-dichloroethane

Conditions

Procedure

Trans-5-amino-2-diphenylmethyl-tetrahydropyran 15 (0.1 g, 0.38 mmol) was reacted with 4-nitrobenzaldehyde (0.057 g, 0.38 mmol) in the presence of glacial acetic acid (0.023 g, 0.38 mmol) in 1,2-dichloroethane (20 ml), and then reduced by NaCNBH3 (0.03 g, 0.45 mmol) in methanol (5 ml) (Procedure D) to give compound 16d (0.12 g, 80%) as an oil.

Source