Aluminium lithium hydride → (S)-tert-butyl (4,4-difluoro-1-hydroxypentan-2-yl)carbamate

Temperature

-10 °C

To a solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)-4,4-difluoropentanoate (70 mg, 0.262 mmol) in tetrahydrofuran (4 mL) at −10° C., was added Lithium aluminum hydride, 2M in THF (0.262 mL, 0.524 mmol). The reaction mixture was stirred at −10° C. for 2 h, then quenched with aqueous ammonium chloride (5 mL) and extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford (S)-tert-butyl (4,4-difluoro-1-hydroxypentan-2-yl)carbamate (38 mg, 0.159 mmol, 61% crude yield) as colorless oil. The material was carried forward without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 3.89 (d, J=4.00 Hz, 2H), 2.10-2.14 (m, 1H), 1.61-1.66 (m, 2H), 1.51 (s, 3H), 1.44 (s, 9H).

1. customquenched with aqueous ammonium chloride (5 mL)
2. extractionextracted with ethyl acetate (2×10 mL)
3. washThe combined organic layers were washed with brine (15 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure

ORD record

ord-7c3920782c404868b1f2373360e59481

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2