Water → HCID 22875341, compound

Participants

Reaction Steps

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.

Provenance & Evidence