Methylamine → ethyl (2S,3R)-3-t-butyldimethylsilyloxy-2-(methylaminomethyl)butanoate

HRID 1975477Notes

Reaction equation

HRID 1975477 reaction equation
[Si:1]([O:8][C@H:9]([CH3:17])[C:10](=[CH2:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:18][NH2:19]>CO>[Si:1]([O:8][C@H:9]([CH3:17])[C@H:10]([CH2:16][NH:19][CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 11108029ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

Product 1

HCID 57178030ethyl (2S,3R)-3-t-butyldimethylsilyloxy-2-(methylaminomethyl)butanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of ethyl (3R)-3-t-butyldimethylsilyloxy-2-methylidenebutanoate (130 g) in methanol (1.3 l) was added a solution of 30% methylamine in methanol (63 ml). The resulting mixture was allowed to stir at ambient temperature for 2 days. Evaporation of the solvent gave ethyl (2S,3R)-3-t-butyldimethylsilyloxy-2-(methylaminomethyl)butanoate (150.0 g).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3ddd4a458c2b4f6b86be2eb0cce87887
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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