Pyrrolidine → HCID 71523248, compound

Participants

Reaction Steps

2-(1-{2-[2-(2-oxopiperidin-1-yl)phenyl]ethyl}pyrrolidin-3-yl)benzoic acid enantiomer 2 a6-8 (2.72 g, 6.97 mmol, 1 eq) is dissolved in dichloromethane (100 ml). Pyrrolidine (0.69 ml, 8.36 mmol, 1.2 eq) is added followed by BOP reagent (Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate; 4.62 g, 10.45 mmol, 1.5 eq) and the reaction mixture is stirred at room temperature for 4 h. The mixture is evaporated to dryness, redissolved in dichloromethane and the organic layer is washed with HCl 1N and water, dried over MgSO4 and evaporated. The residue is purified by reverse phase HPLC (gradient: acetonitrile/H2O/ammonium formate from 5% to 95% of acetonitrile in 8 minutes) to afford 385 mg of (−)-1-[2-(2-{3-[2-(pyrrolidin-1-ylcarbonyl)phenyl]pyrrolidin-1-yl}ethyl)phenyl]piperidin-2-one 17.

Provenance & Evidence