Methanol → (S)-6-(4-bromophenyl)-4-((R)-1-phenylethyl)-[1,4]oxazepane

To a solution of (S)-6-(4-bromophenyl)-4-((R)-1-phenylethyl)-1,4-oxazepan-3-one (1.09 g, 2.91 mmol) in tetrahydrofuran (14.0 ml) was added 1.0M-borane-tetrahydrofuran complex in tetrahydrofuran (6.40 ml, 6.40 mmol) at 0° C. The mixture was stirred at room temperature for 5 hours. After the reaction mixture was cooled to 0° C., methanol (15 ml) and 6.0N-sodium hydroxide (10 ml) was added carefully. The resulting mixture was refluxed for 2 hours and cooled to room temperature. The organic solvent was removed under reduced pressure. The residue was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=7/3) to afford (S)-6-(4-bromophenyl)-4-((R)-1-phenylethyl)-[1,4]oxazepane as white solid (1.00 g, 95%).

1. temperatureAfter the reaction mixture was cooled to 0° C.
2. temperatureThe resulting mixture was refluxed for 2 hours
3. temperaturecooled to room temperature
4. customThe organic solvent was removed under reduced pressure
5. customThe residue was partitioned between saturated ammonium chloride solution and ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel column chromatography (eluant; hexane/ethyl acetate=7/3)

ORD record

ord-fe405b1bbf264e60841b9d56067ac2e0

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108957B2