Acetonitrile → HCID 20694308, compound

Participants

Reaction Steps

A mixture of 1.2 g (3.2 mmol) of 1-Allyl-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(R)-(3-thienyl)pyrrolidine and 0.19 g (0.2 mmol) of Wilkinson's catalyst ([Rh(PPh)3Cl] in 20 mL of an 85% solution of CH3CN in water in a flask fitted with a short path distillation head and an addition funnel for added solvent was heated to reflux. As solvent is azeotroped off, more is added to maintain the original concentration. After stirring at reflux for 4 h, the reaction mixture was concentrated. To the residue was added 3 mL of 2 N HCl and this mixture was partitioned between EtOAc and water. The aqueous fraction was washed with EtOAc and was then made basic with 2 N NaOH solution. The aqueous fraction was then extracted with EtOAc. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated to give the title compound which was used without further purification. Mass Spectrum (CI) m/e=345 (M+1)

Provenance & Evidence