3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 1-(Nicotinoyl)-3-(SR)-((4-phenyl)piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine

Participants

Reaction Steps

A solution of 20 mg (0.06 mmol) of 3-(RS)-((4-phenyl)-piperidin-1-yl)methyl-4-(SR)-phenylpyrrolidine (from Example 30, Step A), 19 mg (0.19 mmol) of TEA and 6 mg (0.05 mmol) of 4-DMAP in 2 mL of CH2Cl2 (2 mL) was treated with 28 mg (0.16 mmol) of nicotinoyl chloride·HCl and was stirred at rt for 2 h. The reaction was concentrated in Vacuo. Preparative thin layer chromatography (silica gel GF, 20×20 cm, 1000 microns) using 92:8 v/v MeOH/CH2Cl2 +0.5% NH4OH as the eluant afforded 20 mg (71%) of the title compound as a yellow foam. 1H NMR (500 MHz, CDCl3): δ7.17-8.88 (9H), 1.27-4.24 (22H). Mass Spectrum (NH3 -CI): 426 (M+1).

Provenance & Evidence