Benzyl Bromide → HCID 71040664, compound

To a stirred solution of (1R,5S)-1-(hydroxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one (3a, 100 mmol, prepared according to Moon, H. R., et al. Nucleosides, Nucleotides and Nucleic Acids, 2007, 26, 975-978) in THF (200 mL) at 0° C. was added NaH (60% in mineral oil, 4.80 g, 120 mmol). After 10 min, BnBr (120 mmol) was added. After stirring at room temperature for 12 h, the reaction was cooled to 0° C., and to the reaction was added saturate aqueous NH4Cl (50 mL) and water (50 mL). The mixture was extracted with ether (300 mL). The organic layer was washed with water (100 mL), brine (50 mL), dried over MgSO4, and concentrated. The residue was purified by column (0-20 ethyl acetate in hanexane) to give a colorless liquid (3b). LCMS (ESI) m/z=219 (M+1).

1. temperaturethe reaction was cooled to 0° C.
2. additionto the reaction was added
3. concentrationsaturate aqueous NH4Cl (50 mL) and water (50 mL)
4. extractionThe mixture was extracted with ether (300 mL)
5. washThe organic layer was washed with water (100 mL), brine (50 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by column (0-20 ethyl acetate in hanexane)

ORD record

ord-14612ee894f74d8995318b2b8615d0a6

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187459B2