Water → HCID 22875341, compound

To a solution of 2.45 g of trans-8-tert-butoxycarbonyl -5-[(1R)-1-phenylethyl]-4-oxo-2-oxa-5,8-diazabicyclo[4.3.0]nonane 9a in 50 ml of tetrahydrofuran, was added 7.1 ml of diborane tetrahydrofuran complex 1M solution dropwise at 0° C. The mixture was stirred at room temperature for 14 hours. Then, 12 ml of diborane tetrahydrofuran complex was added to the solution, and the mixture was stirred at room temperature for 24 hours. To an ice-cooled mixture, was added 10 ml of water and, then, 20 ml of saturated sodium bicarbonate aqueous solution at room temperature. The mixture was stirred at room temperature for 1 hour. The mixture was extracted from 100 ml of ethyl acetate. The organic layer was separated and washed with two 100 ml portions of saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and a residue was subjected to silica gel column chromatography. From an eluant of a mixture of hexane and ethyl acetate (2:1), the titled compound 10a weighing 1.85 g was obtained as an oil.

1. additionThen, 12 ml of diborane tetrahydrofuran complex was added to the solution
2. stirringthe mixture was stirred at room temperature for 24 hours
3. customat room temperature
4. stirringThe mixture was stirred at room temperature for 1 hour
5. extractionThe mixture was extracted from 100 ml of ethyl acetate
6. customThe organic layer was separated
7. washwashed with two 100 ml portions of saturated sodium chloride aqueous solution
8. dry with materialdried over anhydrous sodium sulfate
9. customThe solvent was removed under reduced pressure
10. additionFrom an eluant of a mixture of hexane and ethyl acetate (2:1)
11. customwas obtained as an oil

ORD record

ord-b971b658d68a4eb08819042d44f67a1a

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05654318