Methanol → HCID 59347897, compound

Participants

Reaction Steps

A solution of (±)-1-(2-methyl-1-pyrrolidinyl)cyclopentanecarbonitrile D39 (0.997 g; 5.6 mmol) in dry THF was cooled to −70° C. To this phenyllithium (1.7M in C6H14/ether, 1.1 equiv) was added slowly. The whole mixture was allowed to warm slowly to room temperature over 3 h with stirring under argon. Reaction cooled to 0° C. and methanol added followed by sodium borohydride (portionwise) and allowed to react at 20° C. overnight. The reaction was cooled to 0° C. and quenched with saturated sodium bicarbonate, extracted with ethyl acetate, dried (Na2SO4) and evaporated. The product was purified by chromatography on a 5 g SCX column eluting from 0-100% ethyl acetate in pet. ether, 0-10% methanol in ethyl acetate then 2% 0.880 ammonia in ethyl acetate to give the title compound as an oil (0.67 g; 46%) was obtained. Mass Spectrum (Electrospray LC/MS): Found 259 (MH+). C17H26N2 requires 258. Ret. time 1.19 min.

Provenance & Evidence