Sodium Bromide → tert-butyl N-((2S)-1-oxobutan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2(S)-Boc-aminobutanol (50 g; 264 mmol) in dichloromethane (500 mL) and water (350 mL) were added at 20° C. TEMPO (0.01 eq), sodium bromide (1 eq) and sodium hydrogencarbonate (3 eq). The reaction mixture was stirred at 0° C. and diluted bleach (1.3 eq, 450 mL) was added over 40 min. The reaction mixture was stirred for 30 min. at 0° C. and then quenched with aq. thiosulfate. After decantation and extractions (dichloromethane), the organic phase was washed with brine, dried and concentrated in vacuo to dryness, giving 2(S)-(tert-butoxycarbonyl)aminobutyraldehyde as a low-melting solid (38.1 g; yield: 77%).

Provenance & Evidence