Borane;tetrahydrofuran → (R)-Methyl 4-(4-fluoro-3-methylphenyl)-4-hydroxybutanoate

A solution of BH3.THF (1M, 1.2 mL, 1.2 mmol) was added to 10 mL anhydrous THF followed by the dropwise addition of (S)-2-methyl-CBS-oxazaborolidine (1M, 109 μL, 0.1 mmol) in toluene at 25° C. After stirring for 5 min, methyl 4-(4-fluoro-3-methylphenyl)-4-oxobutanoate (229 mg, 1.0 mmol) was slowly added as a solution in 5 mL THF. The mixture was stirred for 30 min at room temperature and then the reaction was quenched by the careful addition of saturated aqueous ammonium chloride (10 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with brine (2×10 mL) before being dried over Na2SO4. The solvents were removed under reduced pressure and the product isolated by silica gel chromatography to afford the title compound 181 mg, as an oil.

1. stirringThe mixture was stirred for 30 min at room temperature
2. customthe reaction was quenched by the careful addition of saturated aqueous ammonium chloride (10 mL)
3. extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
4. washthe combined organic layers washed with brine (2×10 mL)
5. dry with materialbefore being dried over Na2SO4
6. customThe solvents were removed under reduced pressure
7. customthe product isolated by silica gel chromatography

ORD record

ord-90bd22e7a41145f588d788cc983ffd81

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119692B2