Sodium borohydride → HCID 59382972, compound

Participants

Reaction Steps

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (133 g, 0.32 mol) in 1500 mL methanol was added NaBH4 (73 g, 1.92 mol) at rt. After stirring at rt for 4 h, the solution was evaporated to remove methanol. The remaining solution was treated with water (800 mL), extracted with EtOAc (500 mL×3). The combined organic layers were washed with water (300 mL), dried, filtered, and evaporated to give the desired (S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-hydroxypropan-2-ylcarbamate (102 g, yield 82%). 1H NMR (CDCl3, 400 MHz) δ 0.08 (d, 6H), 0.89 (d, 9H), 1.30 (m, 4H), 1.40 (t, 2H), 1.45 (s, 9H), 1.61 (m, 1H), 1.58 (m, 1H), 1.68 (t, 4H), 1.85 (d, 1H), 3.50 (m, 1H), 3.65 (m, 1H), 3.73 (m, 1H), 3.91 (s, 1H), 4.53 (s, 1H).

Provenance & Evidence