Water → HCID 22875336, compound

To a solution of 3.32 g of cis-8-tert-butoxycarbonyl -5-[(1R)-1-phenylethylamino]-4-oxo-2-oxa-5,8-diazabicyclo[4.3.0]nonane 13b in 6 ml of tetrahydrofuran was added 19.2 ml of 1M diborane tetrahydrofuran complex dropwise under ice-cooling. The mixture was stirred at room temperature overnight. To the mixture was added 5 ml of the diborane solution mentioned above and the mixture was stirred at room temperature for 2 hours. To an ice-cooled reaction mixture was added water and saturated potassium carbonate aqueous solution. The mixture was extracted by ethyl acetate. The organic layer was washed by saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. A residue was subjected to silica gel column chromatography. From an eluant of a mixture of hexane and ethyl acetate (3:1 by volume), the titled compound 14b weighing 2.17 g was obtained.

1. temperaturecooling
2. stirringwas stirred at room temperature for 2 hours
3. customreaction mixture
4. extractionThe mixture was extracted by ethyl acetate
5. washThe organic layer was washed by saturated sodium chloride aqueous solution
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. customthe solvent was removed under reduced pressure
8. additionFrom an eluant of a mixture of hexane and ethyl acetate (3:1 by volume)
9. customwas obtained

ORD record

ord-722ca4a60e2149309cbc0f60f04eea26

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05654318