Lithium borohydride → Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

Participants

Reaction Steps

To a solution of methyl N-(tert-butoxycarbonyl)methioninate (47.7 g, 0.181 mol) in THF (500 mL) was added lithium borohydride (16.0 g, 0.734 mol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 2 hours, the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H22NO3S [M+H]+ 236. found 236. 1H NMR (400 MHz, CD3OD) δ 3.68-3.64 (m, 1H), 3.54-3.47 (m, 2H), 2.59-2.48 (m, 2H), 2.10 (s, 3H), 1.88-1.64 (m, 2H), 1.49 (s, 9H).

Provenance & Evidence