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

HRID 2255660Notes

Reaction equation

HRID 2255660 reaction equation
[Si:1]([O:8][CH: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 14634473Ethyl 2-[1-(t-butyldimethylsilyloxy)ethyl]acrylate

Product 1

HCID 57031907ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoateYield 84.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[1-(t-butyldimethylsilyloxy)ethyl]acrylate (5 g) in methanol (50 ml) was added 4-methoxybenzylamine (2.65 g) at room temperature. After stirring for 2 days, the solvent was removed from the reaction mixture. The residue was column-chromatographed on silica gel in a usual manner (eluent : a mixture of hexane and ethyl acetate, 2:1 to 1:1) to give ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate (6.435 g).

Workup

  1. customthe solvent was removed from the reaction mixture
  2. customThe residue was column-chromatographed on silica gel in a usual manner (eluent
  3. additiona mixture of hexane and ethyl acetate, 2:1 to 1:1)

Sources & evidence

ORD record
ord-ca3606fa8e454cf390dfaa0d3bfbe4c3
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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