Ammonia → HCID 68153470, compound

Participants

Reaction Steps

A solution of (RS)-5-(3-bromo-4-fluoro-phenyl)-5-methyl-morpholin-3-thione (intermediate XVIII-1) (202 mg, 0.7 mmol) in methanol (15 ml) was treated with a solution of ammonia in methanol (7M, 5.7 ml, 39.8 mmol) and an aqueous solution of tert-butyl hydroperoxide (70% in water, 0.91 ml, 6.6 mmol). After stiffing at room temperature overnight, the reaction mixture was diluted with water and extracted three times with dichloromethane. The combined organic layers were washed with water, then dried over sodium sulphate and evaporated. The crude product was purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100/0 to 0/100 as the eluent. The (RS)-5-(3-bromo-4-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine was obtained as a colorless gum (109 mg, 57% of theory). MS (ISP): m/z=287.2 [M+H]+, 289.1 [M+2+H]+.

Provenance & Evidence