L-Alanine → tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

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Reaction Steps

2-(S)-[N-(tert-Butoxycarbonyl)amino]propanal was prepared from L-alanine according to the procedure described in the literature (Chakravarty et al, J. Med. Chem 1989, p1886). A mixture of the aldehyde (2.62 g), dimethylamine hydrochloride (2.47 g), sodium acetate (1.99 g) and sodium cyanoborohydride (1.43 g) in methanol (45 mL) was stirred at room temperature for 8 hours. The reaction mixture was dissolved in ethyl acetate, washed with water, dried (MgSO4), and the solvent removed in vacuo to yield a viscous oil. This was dissolved in dichloromethane, extracted with citric acid, basified with sodium hydroxide, and re-extracted with ethyl acetate. The organic layer was reduced in vacuo to yield the dimethylamino derivative as a white solid (586 mg).

Provenance & Evidence