Sodium borohydride → HCID 15939352, compound

To a solution of 19.33 g (153 mmol) of (1R,3R,5R)-3-hydroxybicyclo[3.2.0]heptan-6-one in 560 mL of dry methanol was added at -78° C. 7.52 g (199 mmol) of sodium borohydride in portions. The reaction mixture was stirred for 2 h and then quenched with 20 mL of saturated ammonium chloride. The mixture was concentrated in vacuo, diluted with 600 mL of ethyl acetate and washed twice with 100 mL of water and 100 mL of brine. The organic layers were dried (MgSO4) and the solvent concentrated in vacuo. The crude product was purified by chromatography on silica gel with petroleum ether (40/60)--ethyl acetate (1:1 v:v). The crude product was recrystallised from hexane to yield 13.70 g (70%) of a colourless solid.

1. customquenched with 20 mL of saturated ammonium chloride
2. concentrationThe mixture was concentrated in vacuo
3. additiondiluted with 600 mL of ethyl acetate
4. washwashed twice with 100 mL of water and 100 mL of brine
5. dry with materialThe organic layers were dried (MgSO4)
6. concentrationthe solvent concentrated in vacuo
7. customThe crude product was purified by chromatography on silica gel with petroleum ether (40/60)
8. customThe crude product was recrystallised from hexane

ORD record

ord-fa141875bc704b8baa0a7376868b9977

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06156935