4-Phenylpiperidine → 1-{[(3S,4S)-1-Benzyl-4-phenyl-3-pyrrolidinyl]methyl}-4-phenylpiperidine

Participants

Reaction Steps

To a solution of 2.68 g (10 mmol) of 1-benzyl-3-(R)-formyl-4-(S)-phenylpyrrolidine in 10 mL of 1,2-dichlorethane was added 2.0 g (12 mmol) of 4-phenylpiperidine. To this was added 3.2 g (15 mmol) of sodium triacetoxyborohydride and the solution was stirred at room temperature for 1 h. The reaction was poured into 50 mL of saturated NaHCO3 solution and the mixture was extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel using ethyl acetate-hexane (1:1) to afford the title compound. 1H NMR (CDCl3) δ 1.6-1.85 (m, 4H), 1.98 (dq, J=7 Hz, J=2 Hz, 2H), 2.4-2.56 (m, 4H), 2.62 (m, 1H), 2.72 (m, 1H), 2.83 (m, 1H), 3.04 (m, 4H), 3.69 (d, AB, J=7 Hz, 1H), 3.77 (d, AB, J=7 Hz, 1H), 7.2-7.6 (m, 15H); Mass Spectrum (ESI) m/e 411 (M+1); [α]D =+26.0 (c.=1.56, CHCl3)

Provenance & Evidence