Lithium borohydride → HCID 11339552, compound

Temperature

25 °C

To a solution of ethyl N-[(5-bromo-thien-2-yl)sulfonyl]-4,4,4,4′,4′,4′-hexafluorovalinate (2.4 g, 5.02 mmol) in THF (20 mL) was added LiBH4 (20 mL, 20.07 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. and quenched with 2N HCl (slow addition), diluted in ether (50 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 (2.31 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:6 EtOAc-hexanes, to afford 5-bromo-N-[3,3,3-trifluoro-1-(hydroxymethyl)-2-(trifluoromethyl)propyl]thiophene-2-sulfonamide as a white solid (1.3 g, 59.63%). Mass Spectrum (−ESI): 435 (M−H)−.

1. temperatureThe reaction was cooled to 0° C.
2. customquenched with 2N HCl (slow addition)
3. additiondiluted in ether (50 mL)
4. washthe organic layer was washed sequentially with 1N aqueous
5. dry with materialHCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL), then dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customto obtain a crude oil (2.31 g)
9. customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

ORD record

ord-317dcc8b367540cdbc4a6cde83d747e7

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858658B2