Tetrahydrofuran → HCID 58692303, compound

Participants

Reaction Conditions

Reaction Steps

3,4-Dimethylmagnesium bromide (250 mL of a 0.5 M solution in tetrahydrofuran, 125 mmol, Rieke Metals, Inc., 3045) was added to a suspension of copper (I) cyanide (5.48 g, 61.2 mmol) in anhydrous tetrahydrofuran (400 mL) under nitrogen at approximately −50° C. After stirring at approximately −50° C. for 10 minutes, the reaction mixture was allowed to warm to ambient temperature over 1 h then recooled to approximately −50° C. A solution of tert-butyl 4-(1-cyano-2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate 8-2 (15.0 g, 51.0 mmol) in tetrahydrofuran (50 mL) was added. After stirring at −50° C. for 3 h, the reaction mixture was warmed to 0° C. and quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried (magnesium sulfate) and concentrated in vacuo to give compound 8-3 as light yellow oil.

Provenance & Evidence