Benzylamine → ethyl (2S,3R)-2-aminomethyl-3-(t-butyldimethylsilyloxy)butanoate

HRID 2255668Notes

Reaction equation

HRID 2255668 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].C([NH2:25])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:25][CH2:17][C@@H:11]([C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])[CH3:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 11108029ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

Product 1

HCID 11054926ethyl (2S,3R)-2-aminomethyl-3-(t-butyldimethylsilyloxy)butanoateYield 101.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate (25.84 g) in methanol (517 ml) was added benzylamine (11.79 g) at room temperature. After stirring for 6 days, 10% palladium hydroxide on carbon (2.58 g) was added and the mixture was stirred under hydrogen atmosphere for 5 hours. After the termination of reaction, the mixture was concentrated to give crude ethyl (2S,3R)-2-aminomethyl-3-(t-butyldimethylsilyloxy)butanoate (28.02 g). This compound was immediately used as the starting compound for the next transformation without further purification.

Workup

  1. stirringthe mixture was stirred under hydrogen atmosphere for 5 hours
  2. customAfter the termination of reaction
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-ae125daf4b294d0b9611b200081c8a1b
Source dataset
uspto-grants-1993_08
Patent number
US05241064

Reaction notes

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