Sodium Hydroxide → (1S,5R)-1-Amino-7-methylene-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane

Temperature

80 °C

A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (0.539 ml, 1.79 mmol) was added to a solution of (1S,5S)-1-amino-7-methylene-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]octane (115 mg, 0.449 mmol) in toluene (2.24 ml), and the mixture was stirred at room temperature for 30 minutes and at 80° C. for 30 minutes. A 5 mol/l sodium hydroxide solution (15.0 ml) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 ml×1, 20 ml×1). The organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 106 mg of the title compound.

1. stirringwith stirring under ice-
2. temperaturecooling
3. extractionfollowed by extraction with toluene (30 ml×1, 20 ml×1)
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-194f4f36d0ae434cb658a771db19d65e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2