Methanol → HCID 67281263, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-bromo-phenyl)-4-((R)-1-phenyl-ethyl) -[1,4]oxazepan-3-one (diastereomer 1) (9.39 g, 25.1 mmol) in tetrahydrofuran (75 ml) was added 1.0M-borane-tetrahydrofuran complex in tetrahydrofuran (75.0 ml, 75.0 mmol) at 0° C. The mixture was refluxed for 4 hours. The mixture was cooled to 0° C. and methanol (100 ml) and 6.0 N aqueous sodium hydroxide (100 ml) was added carefully. The mixture was refluxed for 2 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The organic layer was washed with brine, dried over sodium sulfate, concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=4/1) to afford diastereomerically pure 2-(3-bromophenyl)-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane as colorless oil (8.92 g, 99%).

Provenance & Evidence