Methanol → HCID 66975625, compound

Temperature

60 °C

To a solution of (6RS,7SR)-4-benzyl-7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-6-(3,4-dichlorophenyl)-1,4-oxazepan-3-one (3.11 g) in THF (20 mL) was added 1 M THF solution (13.8 mL) of borane-THF complex at 0° C., and the mixture was stirred at 60° C. for 2 hr. To the reaction mixture was added methanol, and the solvent was evaporated under reduced pressure. To the residue was added 6 N hydrochloric acid (8 mL), and the reaction mixture was stirred at 60° C. overnight. The reaction mixture was basified with 8 N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.22 g).

1. customthe solvent was evaporated under reduced pressure
2. additionTo the residue was added 6 N hydrochloric acid (8 mL)
3. stirringthe reaction mixture was stirred at 60° C. overnight
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-aa643ac4203b42d9bdaaef914bf195de

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2