Borane;tetrahydrofuran → (R)-Methyl 4-(4-fluorophenyl)-4-hydroxybutanoate

To a solution of BH3.THF (1M, 5.7 mL, 5.7 mmol) in 40 mL anhydrous THF was dropwise added at room temperature (S)-2-methyl-CBS-oxazaborolidine (952 μL, 0.952 mmol, 1M in toluene). After stirring for 5 minutes, methyl 4-(4-fluorophenyl)-4-oxobutanoate (2.0 g, 9.5 mmol) was added as a solution in 25 mL THF. The reaction mixture was stirred for 30 min at room temperature and then quenched by the slow addition of saturated aqueous ammonium chloride (60 mL) The resulting mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers washed with brine (2×40 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the product isolated by silica gel Flash chromatography to afford 1.7 g of the title compound as a colorless oil.

1. stirringThe reaction mixture was stirred for 30 min at room temperature
2. customquenched by the slow addition of saturated aqueous ammonium chloride (60 mL) The resulting mixture
3. extractionwas extracted with ethyl acetate (3×50 mL)
4. washthe combined organic layers washed with brine (2×40 mL)
5. dry with materialdried over Na2SO4
6. customThe solvent was evaporated under reduced pressure
7. customthe product isolated by silica gel Flash chromatography

ORD record

ord-91d79123319844f48e197572dc72393a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119692B2