Hydrogen Peroxide → 2-[(1R,2S)-2-(4-Bromophenyl)cycloprop-1-yl]ethanol

To a solution of the alkene from Example 28D (1-bromo-4-[(1S,2R)-2-vinylcyclopropyl]benzene) in anhydrous THF (50 mL) under N2 was added borane-THF at 0° C. The mixture was stirred at room temperature for two hours and then chilled to 0° C. Aqueous hydrogen peroxide (30%) solution was added, the ice bath was removed, and the mixture was allowed to warm to room temperature with continued stirring for 10 minutes. The mixture was quenched with saturated aqueous NH4Cl and extracted with ether. The combined organic extracts were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified on silica gel with 4:1 hexanes/ethyl acetate to provide the title compound.

1. temperaturechilled to 0° C
2. customthe ice bath was removed
3. temperatureto warm to room temperature
4. stirringwith continued stirring for 10 minutes
5. customThe mixture was quenched with saturated aqueous NH4Cl
6. extractionextracted with ether
7. dry with materialThe combined organic extracts were dried (MgSO4)
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. customThe residue was purified on silica gel with 4:1 hexanes/ethyl acetate

ORD record

ord-f745d5fda73a4cd4a2c1b3e21b07a63b

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829041B2