Cesium fluoride → HCID 66724999, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4R)-4-(2-iodo-4-chlorophenyl)pyrrolidin-2-one (600 mg, 1.8 mmol), copper(I) iodide (36 mg, 0.18 mmol) and Pd(Ph3P)4 (103 mg, 0.09 mmol) in DMF (5 mL) under a nitrogen atmosphere was introduced vinyl tributyl tin (0.68 g, 2.16 mmol) followed by CsF (54 0 mg, 3.6 mmol). The reaction mixture was heated overnight at 100° C. After the reaction mixture was cooled to room temperature, it was diluted with water and extracted with ethyl ether (3×30 mL). The combined organic phases were washed with a 1N HCl aq. solution, a saturated sodium bicarbonate aqueous solution, and brine. The organic phase was then dried over sodium sulfate and concentrated in vacuo to provide (4R)-4-(4-chloro-2-vinylphenyl)pyrrolidin-2-one (0.35 g, 85% crude yield); MS (ESI) m/z 222.04 (M+H)+. (4R)-4-(4-Chloro-2-vinylphenyl)pyrrolidin-2-one (75 mg, 0.33 mmol) was treated overnight with a 6N HCl aq. solution at 90° C. The product was purified by HPLC to provide the title compound. MS (ESI) m/z 240.06 (M+H)+.

Provenance & Evidence