Methanol → 1-Propanol, 2-amino-3-(dimethylamino)-, hydrochloride (1:2), (2S)-
Reaction equation
[ClH:1].[CH3:2][NH:3][CH3:4].[C:5]([BH3-])#[N:6].[Na+].[C:9]([O-])(=[O:11])C.[Na+].[CH3:14]O>>[ClH:1].[NH2:6][C@@H:5]([CH2:2][N:3]([CH3:14])[CH3:4])[CH2:9][OH:11]Participants
Procedure
N-[(tert-Butoxy)carbonyl]-O-(tert-butyldimethylsilyl)-R-serine methyl ester was prepared according to the literature (H. W. Scheeren et al, J. Org. Chem. 1990, p3998) from D-serine methyl ester hydrochloride. Treatment of this compound with diusobutyl aluminium hydride in toluene at −70° C. for 2 hours yielded the corresponding aldehyde (H. W. Scheeren et al, J. Org. Chem. 1990, p3998). A mixture of the crude aldehyde (4.43 g), dimethylamine hydrochloride (2.26 g), sodium cyanoborohydride (1.31 g) and sodium acetate (1.83 g) was stirred in methanol (55 mL) for 24 hours at room temperature. Aqueous work-up yielded the dimethylamine derivative. This was dissolved in dioxane and to this was added a 4.0 M solution of hydrochloric acid in dioxane and the mixture stirred for 20 minutes. Concentration of the mixture in vacuo yielded the crude desired title compound as a white solid.
Sources & evidence
- ORD record
- ord-ce0f48873c214f2e8a0b273c1fbd69ca
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552021B2
Reaction notes
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