Sodium Bromide → (S)-2-Boc-aminobutyraldehyde

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To a solution of (S)-2-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 (S)-2-(tert-butoxycarbonyl)-amino-butyraldehyde as a low-melting solid (38.1 g; yield: 77%). C9H17NO3; MW=187.2; Tmelt=44° C.; NMR (CDCl3, ppm): 0.97 (t, J=7 Hz, 3H), 1.45 (s, 9H), 1.68 (m, 1H), 1.91 (m, 1H), 4.20 (lq, J=6.5 Hz, 1H), 5.09 (1s, 1H (mobile)) and 9.59 (s, 1H); SM (EI; m/z): 158 (M+—CHO), 102, 57.

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