Tetrahydrofuran → 1-[2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxy-benzyl)-pyrrolidin-3-yl]-ethyl]-4-phenyl-piperidine-4-carboxylic acid amide

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Reaction Steps

Combine 4-phenyl-piperidine-4-carboxylic acid-amide hydrochloride (0.5 g, 2.1 mmol), 1-(3,4,5-trimethoxybenzyl)-3-(3,4-dichloro-phenyl)-3-(2-oxo-ethyl)-pyrrolidine (0.23 g, 0.53 mmol), and titanium(IV) isopropoxide (0.2 g, 0.7 mmol) in methanol (5 mL). Add a solution of sodium cyanoborohydride in tetrahydrofuran (0.9 mL, 1M, 0.9 mmol). After 18 hours, a precipitate had formed. Filter, rinse with methanol and dichloromethane, and evaporate the filtrate to give a residue. Combine residue with dichloromethane and an aqueous 2M solution of potassium hydroxide. Separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, dichloromethane/methanol/concentrated ammonia (196/4/0.2), dichloromethane/methanol/concentrated ammonia (242/8/0.4), and then dichloromethane/methanol/concentrated ammonia (238/12/0.6) to give the title compound. Elemental Analysis calculated for C34H43 Cl2N3O4.0.4 H2O: C 64.52; H 6.64; N 6.64. Found C 64.15; H 6.33; N 6.67.

Provenance & Evidence