Sodium borohydride → HCID 59382972, compound

Participants

Reaction Steps

To a solution of tert-butyl (S)-1-(methoxycarbonyl)-2-(4-(t-butyldimethylsilyloxy)-cyclohexyl)ethylcarbamate (25 g, 60 mmol) in EtOH (500 mL) at 0° C. was added NaBH4 (18 g, 480 mmol) in portions. The mixture was stirred for 6 h at rt and then evaporated. The residue was partitioned between water (200 mL) and EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, and evaporated to give (2S)-2-(t-butoxycarbonylamino)-3-(4-(t-butyldimethylsilyloxy)cyclohexyl)propan-1-ol (23 g, yield 98%). 1H NMR (CDCl3, 400 MHZ) δ 0.08(d, 6 H), 0.89(d, 9 H), 1.30(m, 4 H), 1.40 (t, 2 H), 1.45 (s, 9 H), 1.61(m, 1H), 1.58 (m, 1 H), 1.68 (t, 4 H), 1.85 (d, 1 H) 3.50 (m, 1 H), 3.65 (m, 1 H), 3.73 (m, 1 H), 3.91 (s, 1 H), 4.53(s, 1 H).

Provenance & Evidence