Lithium borohydride → HCID 11328901, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl N-[(4-bromo-5-chloro thien-2-yl)sulfonyl]-4,4,4,4′,4′,4′-hexafluorovalinate (1.45 g, 2.907 mmol) in THF (20 mL) was added lithium borohydride (LiBH4) (5.82 mL, 11.64 mmol) under N2 atmosphere at 0° C. The reaction was allowed to warm to 25° C. for 19 h. The reaction was cooled to 0° C., quenched with 2N HCl (slow addition), diluted in ether (40 mL) and the organic layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL), then dried over MgSO4, filtered and concentrated to obtain a crude oil (1.3 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:6 EtOAc-hexanes, to afford 4-bromo-5-chloro-N-[3,3,3-trifluoro-1-(hydroxymethyl)-2-(trifluoromethyl)propyl]thiophene-2-sulfonamide as a white solid (1.13 g, 84.32%). Mass Spectrum (−ESI): 469 (M−H)−.

Provenance & Evidence