4-Benzyl-5-methyl-[1,4]oxazepan-3-one → 4-Benzyl-5-methyl-[1,4]oxazepane

To a solution of 4-benzyl-5-methyl-[1,4]oxazepan-3-one (0.32 g, 1.4 mmol) in tetrahydrofuran (5 mL) was added 1M solution of boran-tetrahydrofran complex in tetrahydrofuran (5 mL, 5.0 mmol) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 3 hours. Then the reaction was quenched by the addition of methanol and the solution was concentrated. The residual oil was dissolved in methanol (10 mL) and 1M sodium hydroxide aqueous solution was added at room temperature. The mixture was refluxed for 3 hours and diluted with water. Extraction with ethyl acetate was performed and the organic extracts were dried over anhydrous sodium sulfate. After evaporation of solvents, the residue was purified by flash column chromatography on silica gel to yield 4-benzyl-5-methyl-[1,4]oxazepane (0.30 g, 1.4 mmol, 100%) as colorless oil.

1. customThen the reaction was quenched by the addition of methanol
2. concentrationthe solution was concentrated
3. dissolutionThe residual oil was dissolved in methanol (10 mL)
4. addition1M sodium hydroxide aqueous solution was added at room temperature
5. temperatureThe mixture was refluxed for 3 hours
6. additiondiluted with water
7. extractionExtraction with ethyl acetate
8. dry with materialthe organic extracts were dried over anhydrous sodium sulfate
9. customAfter evaporation of solvents
10. customthe residue was purified by flash column chromatography on silica gel

ORD record

ord-5dce31e93ef24052b61c4d955ee83513

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108957B2