Sodium Hydroxide → HCID 15454896, compound

Participants

Reaction Steps

To a stirred solution of (2S*,3S*,4S*,5R*)-3-amino-1-benzyloxycarbonyl-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (793 mg, 2.15 mmol) and 2-methoxy-5-trifluoromethoxybenzaldehyde (569 mg, 2.58 mmol) in dry CH2Cl2 (10 ml) was added NaBH(OAc)3 (639 mg, 3.01 mmol) portionwise at room temperature. After stirring for 2 h at room temperature, the reaction mixture was basified to pH 10-11 by adding 10% NaOH aq. solution with ice-cooling. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (60 ml×4). The combined CH2Cl2 solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude title compound (1.32 g) as a yellow viscous oil. This was purified by column chromatography on silica gel (65 g) with hexane-ethyl acetate (3:1-2:1) to give the pure title compound (1.08 g, 88%) as a pale yellow oil.

Provenance & Evidence