Lithium borohydride → HCID 86710445, compound

Participants

Reaction Conditions

Reaction Steps

An ambient temperature solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)-5,5-difluoropent-4-enoate (1.91 g, 7.20 mmol) in tetrahydrofuran (25 mL) was treated with lithium borohydride (0.31 g, 14 mmol) and stirred for 1 h. The resulting solution was cooled to 5° C., quenched with 0.1 N aqueous hydrochloric acid (50 mL), and extracted with ethyl acetate (3×25 mL). The pooled organic extracts were washed with brine (1×20 mL), dried over MgSO4, and concentrated under reduced pressure. The crude material was purified over SiO2 (20-100% ethyl acetate/hexanes gradient elution) to afford (S)-tert-butyl (5,5-difluoro-1-hydroxypent-4-en-2-yl)carbamate (1.4 g, 5.90 mmol, 82% yield) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.75 (d, J=6.0 Hz, 1H), 4.35-4.05 (m, 1H), 3.82-3.51 (m, 3H), 2.46-2.16 (m, 3H), 1.47 (s, 9H).

Provenance & Evidence