Methanol → Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate

Participants

Reaction Steps

To a solution R—CBS (20.2 mL, 20.2 mmol) and BH3.Me2S (30.3 mL, 303 mmol) in THF (250 mL) was added a solution of tert-butyl 3-(3-chlorophenyl)-3-oxopropyl(methyl)carbamate (60 g, 0.202 mol) in THF (300 mL) at −15° C. After addition, the mixture was stirred at room temperature for 1 hour. Methanol was added drop wise carefully at −15° C. The solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel eluting with AcOEt/petroleum ether (1:15→1:8) to provide the light yellow oil. 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 9H), 1.70 (m, 1H), 1.94 (m, 1H), 2.87 (s, 3H), 3.01 (m, 1H), 3.96 (m, 1H), 4.52 (m, 1H), 7.26 (m, 4H).

Provenance & Evidence