Hydrochloric Acid → HCID 67282402, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-benzylamino-2-(4-bromophenyl)propionate (7.1 g, 20.5 mmol) in toluene (40 mL) at 0° C. under nitrogen atmosphere was added a 1M solution of diisobutylalminium hydride (DIBAH) in toluene (65 mL, 65 mmol) and the resulting mixture was stirred for 3 hours. After cooling to 0° C., sodium fluoride (10.9 g, 260 mmol) and water (3.5 mL, 195 mmol) was added to quench aluminum reagents. The white slurry was stirred for 30 minutes and filtered to remove solid materials. The organic solution was concentrated. The resulting residue was diluted with dichloromethane (80 mL) and cooled to 0° C. To the solution was added triethylamine (4.2 mL, 30 mmol) and chloroacetyl chloride (1.6 mL, 20 mmol) and stirred for one hour. The reaction mixture was poured into 1N hydrochloric acid aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The viscous residual oil was dissolved in 2-propanol (50 mL) and then potassium hydroxide pellet (2 g, 30 mmol) was added at room temperature. After vigorous stirring over night, the reaction solution was diluted with water and extracted with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate and concentrated. The residual material was purified by flash column chromatography on silica gel (hexane/ethyl acetate=3/1 as an eluant) to afford 4-benzyl-6-(4-bromo-phenyl)-[1,4]oxazepan-3-one (3.0 g, 8.3 mmol, 41%) as brown oil.

Provenance & Evidence