Sodium hydride → HCID 15908912, compound

Participants

Reaction Steps

To a 1000 mL 3-necked round-bottomed flank equipped with addition funnel and nitrogen inlet was added 3.9 grams (97.6 mmol) sodium hydride, which was then washed with hexane, and 400 mL dry tetrahydrofuran. To the stirring suspension was added a solution of 31.8 grams (88.8 mmol) 3-Bromo-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-2-one and 23.5 grams (97.6 mmol) t-butyl iodoacetamide. The reaction was stirred at room temperature for 60 hours, quenched with ammonium chloride solution, then poured into water, extracted twice into ethyl acetate, washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 2/1-hexane/ethyl acetate an eluent to afford 38.7 grams (92%) of a foam, a mixture of diastereomers.

Provenance & Evidence