4-Phenylpiperidine → 1-phenylmethyl-3-(SR)-((4-phenyl) piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

A solution of 680 mg (2.6 mmol) of 1-phenylmethyl -3-(RS)-formyl -4-(SR)-phenylpyrrolidine (from Example 9, Step B) and 420 mg (2.6 mmol) of (4-phenyl)piperidine in 25 mL of dichloroethane at 0° C. was treated with 635 mg (3.0 mmol) of sodium triacetoxy-borohydride. The cooling bath was removed and the resulting mixture was stirred at rt for 2h. The reaction mixture was partitioned between 100 mL of EtOAc and 50 mL of sat'd NaHCO3 and the layers were separated. The organic layer was washed with 50 mL of sat'd NaCl, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 50 g of silica gel using 10:1 v/v hexanes/EtOAc+1% TEA as the eluant afforded 1.01 g of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ1.65-2.02 (6H.), 2.42-3.03 (11H), 3.72 (AB q, J=35.4, 2H), 7.20-7.43 (m, 15H). Mass Spectrum (NH3 -CI): 411 (M+1).

Provenance & Evidence