Ethanol → HCID 67490995, compound

{(1S,5R,6R)-6-Fluoro-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3,3,0]octan-1-yl}carboxylic acid tert-butyl ester (420 mg, 1.21 mmol) was dissolved in tetrahydrofuran (20 mL), and a 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was added dropwise in a nitrogen atmosphere. After five hours, a 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was added; after 15 hours, a 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was further added. After stirring for three hours, ethanol (18 mL), water (2 mL), and triethylamine (2 mL) were added, and the mixture was stirred at 80° C. for two hours. The reaction solution was evaporated under reduced pressure, and a saturated ammonium chloride solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in dichloromethane (3 mL). Benzyloxycarbonyl chloride (1.03 g, 6.04 mmol) was added, and the mixture was stirred for 16 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give 367 mg of the title compound as a colorless oil.

1. additiona 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was added dropwise in a nitrogen atmosphere
2. additiona 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was added
3. waitafter 15 hours
4. additiona 1 M borane-tetrahydrofuran complex (3.63 mL, 3.63 mmol) was further added
5. stirringthe mixture was stirred at 80° C. for two hours
6. customThe reaction solution was evaporated under reduced pressure
7. additiona saturated ammonium chloride solution was added to the resulting residue
8. extractionfollowed by extraction with ethyl acetate
9. washThe organic layer was washed with water and brine
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationAfter filtration
12. customthe solvent was evaporated under reduced pressure
13. dissolutionthe resulting residue was dissolved in dichloromethane (3 mL)
14. stirringthe mixture was stirred for 16 hours
15. concentrationThe reaction solution was concentrated under reduced pressure
16. customthe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

ORD record

ord-1aa752a861ad4946bd0dc3261fcfb6c1

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2