Lithium borohydride → 5-Chloro-n-[4,4,4-trifluoro-1-(hydroxymethyl)-2-(2,2,2-trifluoroethyl)butyl]thiophene-2-sulfonamide

HRID 1985971노트

반응식

HRID 1985971 반응식
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([C:23](OC)=[O:24])[CH:12]([CH2:18][C:19]([F:22])([F:21])[F:20])[CH2:13][C:14]([F:17])([F:16])[F:15])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][CH:11]([CH2:23][OH:24])[CH:12]([CH2:18][C:19]([F:20])([F:22])[F:21])[CH2:13][C:14]([F:16])([F:15])[F:17])(=[O:8])=[O:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 86594495methyl N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-dl-norvalinate

생성물 1

HCID 114300705-Chloro-n-[4,4,4-trifluoro-1-(hydroxymethyl)-2-(2,2,2-trifluoroethyl)butyl]thiophene-2-sulfonamide수율 2.36%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

To a solution of methyl N-[(5-chlorothien-2-yl)sulfonyl]-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-dl-norvalinate (0.5 g, 1.11 mmol) in THF (10 mL) was added LiBH4 (2.28 mL, 4.46 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 (40 mL) and the organic layer 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 (0.362 g). The crude product was purified by the Biotage Flash™ 12 chromatography system, eluent: 1:6 EtOAc-hexanes, to afford 5-chloro-N-[4,4,4-trifluoro-1-(hydroxymethyl)-2-(2,2,2-trifluoroethyl)butyl]thiophene-2-sulfonamide as a colorless oil (0.001 g, 2.36%). Mass Spectrum (−ESI): 418 (M−H)−.

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 2N HCl (slow addition)
  3. additiondiluted in ether (40 mL)
  4. washthe organic layer washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a crude oil (0.362 g)
  9. customThe crude product was purified by the Biotage Flash™ 12 chromatography system, eluent

출처 및 근거

ORD 기록
ord-c98acfb62300461bb6323d476e415c6f
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547725B2

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