Borane → 2,2'-(Cyclopentane-1,1-diyl)di(ethan-1-ol)

To a stirred solution of (1-carboxymethyl-cyclopentyl)-acetic acid (1.0 g, 5.3 mmol) at 0° C. was added borane in THF (20 mL, 1.0 M; 20 mmol) and the resultant reaction mixture was stirred and allowed to come to RT overnight. The reaction mixture was cooled in an ice bath and quenched by dropwise addition of methanol (about 5 mL). The solvent was evaporated under reduced pressure and the residue was partitioned between aqueous sodium bicarbonate and ethyl acetate (about 50 mL, 1:1). The organic phase was dried over Na2SO4, concentrated under reduced pressure and filtered through a bed of silica gel to afford 2-[1-(2-hydroxy-ethyl)-cyclopentyl]-ethanol (800 mg) after evaporation of the eluent.

1. customthe resultant reaction mixture
2. temperatureThe reaction mixture was cooled in an ice bath
3. customquenched by dropwise addition of methanol (about 5 mL)
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was partitioned between aqueous sodium bicarbonate and ethyl acetate (about 50 mL, 1:1)
6. dry with materialThe organic phase was dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. filtrationfiltered through a bed of silica gel

ORD record

ord-40e8d47371544920bf46abbfcc05e740

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563742B2