HCID 15454897, compound → HCID 70300060, compound

Participants

Reaction Steps

20% Pd(OH)2 --C (Pearlman's cat., 600 mg) was added to a solution of (2S*,3S*,4S*,5R*)-1-benzyloxycarbonyl-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine 1.08 g, 1.89 mmol) and HCO2NH4 (714 mg, 11.3 mmol) in methanol (25 ml). The reaction mixture was stirred and heated at a gentle reflux for 30 min. The catalyst was filtered off by the aid of a Celite pad, and washed with MeOH. The combined filtrate and washings were concentrated in vacuo. The residue was basified to pH 10-11 with 10% NaOH aq. solution, and extracted with CH2Cl2 (60 ml×4). The combined CH2Cl2 extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give a crude mixture of (2S*,3S*,4R*,5R*)-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine and (2S*,3S*,4R*,5R*)-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (794 mg) as a yellow oil. This was purified by column chromatography on silica gel (45 g) with hexane-ethyl acetate (1:1) to give (2S*,3S*,4S*,5R*)-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (222 mg, 27.3%) as a pale yellow solid, which was recrystallized from hexane-ethyl acetate to give (2S*,3S*,4S*,5R*)-3-[N-(2-methoxy-5-trifluoromethoxybenzyl)-amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (127 mg, 1st crop) as a white solid: mp 81-82° C.

Provenance & Evidence