Ammonia → HCID 86724981, compound

Participants

Reaction Steps

Under a nitrogen gas atmosphere, metallic sodium (920 mg, 40.0 mmol) was added to liquid ammonia (about 30 ml) at −78° C. over a period of 5 minutes, and the mixture was further stirred at the same temperature for 15 minutes. To the reaction solution, a solution of (4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1R)-1-phenylethyl]pyrrolidin-2-one (Heterocycles, 2003, vol. 60, No. 11, pages 2485-2498, or synthesized with reference to JP09136886; 3.34 g, 10.0 mmol) in tetrahydrofuran (10 ml)/tert-butyl alcohol (1 ml) was added over a period of 5 minutes and the mixture was stirred for about 1 hour. Ammonium chloride (3.21 g) was added thereto, and ammonia was evaporated by gradually raising the temperature to room temperature when the color of the reaction solution changed from dark blue to colorless. Water was added to dissolve the insoluble material and the resultant was extracted with a mixed solution of chloroform-methanol (9:1). The organic layer was dried over anhydrous sodium sulfate, the drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to yield 2.29 g (100%) of the title compound in the form of a colorless oily product.

Provenance & Evidence