Trimethylsilyl cyanide → HCID 86620141, compound

Participants

Reaction Steps

A solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-yl]carbamate (0.67 g, 1.97 mmol) in tetrahydrofuran (10 mL) was slowly added to a solution of zirconocene chloride hydride (0.76 g, 2.95 mmol) in tetrahydrofuran (5.0 mL) at −20° C. After 15 min, the mixture was allowed to warm to ambient temperature. After 3 h, trimethylsilanecarbonitrile (1.31 mL, 9.84 mmol) was added. After 16 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with Rochelle's salt (1.0 M in water), brine, dried over sodium sulfate, filtered, and concentrated. MS 352.1 (M+1).

Provenance & Evidence