4-Methoxybenzylamine → ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate

HRID 2255665Notes

Reaction equation

HRID 2255665 reaction equation
[Si:1]([O:8][C@@H:9]([C:11](=[CH2:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>CO>[Si:1]([O:8][C@H:9]([CH3:10])[C@H:11]([CH2:17][NH:25][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 11108029ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

Product 1

HCID 57031907ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoateYield 109.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate (15 g) in methanol (300 ml) was added 4-methoxybenzylamine (8.05 g) at room temperature. After stirring for 2 days, the solvent was removed by evaporation to give crude ethyl (2S,3R)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate (25.14 g).

Workup

  1. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-24f5b77d1929463b99f39f7eba3896d4
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

Loading…