Sodium Hydroxide → (3R)-α,α-Diphenyl-3-pyrrolidineacetamide

Participants

Reaction Conditions

Reaction Steps

3-(R)-(-)-(1-cyano-1,1-diphenylmethyl)pyrrolidine (9.2 g--see Preparation 9(B)) was dissolved in 95% sulphuric acid (80 ml) and the mixture was heated at 80° C. for 4 hours and then at 90° C. for 1 hour. Ice (1 kg) was added and the mixture was basified (pH 12) by the addition of a cold solution of sodium hydroxide (120 g) in water (100 ml). The mixture was extracted with dichloromethane (4×100 ml) and the combined extracts were dried (MgSO4) then concentrated in vacuo to give a foam which was purified by column chromatography on alumina eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a foam, yield, 4.5 g, [α]D25 +16.9° (c 1.0, CH2Cl2).

Provenance & Evidence