Ethyl Acetate → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

Participants

Reaction Steps

2-(R)-[N-(tert-Butoxycarbonyl)amino]propanal was prepared from D-alanine Me-ester hydrochloride according to the procedure described in the literature (Chakravarty et al, J. Med. Chem 1989, p1886). A mixture of the aldehyde (16.21 g), dimethylamine hydrochloride (15.28 g), sodium acetate( 1.53 g) and sodium cyanoborohydride (8.24 g) in methanol (250 mL) was stirred at room temperature for 18 hours maintaining pH at 6-7 with AcOH. The reaction mixture was dissolved in ethyl acetate, washed with water, dried (MgSO4), and the solvent removed in vacuo to yield a viscous oil which was purified using flash chromatography to yield the dimethylamino derivative as a white solid (10.81 g).

Provenance & Evidence