Hydrochloric Acid → HCID 58155211, compound

Participants

Reaction Conditions

Reaction Steps

A dispersion of N-[(R)-1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1,2-dimethyl-propyl]-2-chloro-acetamide (2.79 g, 7.91 mmol) in toluene (80 ml) at 23° C. was treated dropwise with a solution of potassium amylate (1.7 M in toluene, 24 ml, 41 mmol) within 30 minutes (slightly exothermic reaction). After complete addition the mixture was stirred at 23° C. for 45 minutes. For the workup, the reaction mixture was poured into hydrochloric acid (1M) and extracted with ethyl acetate. The organic layer was separated and washed with a saturated sodium hydrogen-carbonate solution and brine. The combined aqueous layers were re-extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, then evaporated at reduced pressure to yield light brown oil. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate as the eluent. The (R)-5-(5-bromo-2-fluoro-phenyl)-5,6,6-trimethyl-morpholin-3-one was obtained as a light yellow gum (1.83 g, 73% of theory). Mass (calculated) C13H15BrFNO2 [316.168]; (found) [M+H]+=316, [M+2-H]+=318.

Provenance & Evidence