Lithium borohydride → 3,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamide

HRID 1987588노트

반응식

HRID 1987588 반응식
C([O:3][C:4](=O)[CH:5]([NH:15][S:16]([C:19]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=1)(=[O:18])=[O:17])[CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([F:10])([F:9])[F:8])C.[Li+].[BH4-]>C1COCC1>[F:25][C:23]1[CH:24]=[C:19]([S:16]([NH:15][CH:5]([CH2:4][OH:3])[CH:6]([C:7]([F:10])([F:8])[F:9])[C:11]([F:12])([F:13])[F:14])(=[O:17])=[O:18])[CH:20]=[C:21]([F:27])[C:22]=1[F:26]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 866160084,4,4-Trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester

생성물 1

HCID 247659453,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamide수율 30.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

To a solution of 4,4,4-trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester (0.54 g, 1.207 mmol) in THF (10 mL) was added LiBH4 in THF (2.40 mL, 4.81 mmol) 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), and diluted with Et2O (40 mL). The organic layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL), dried over MgSO4, filtered and concentrated to obtain a crude oil (0.49 g). The crude product was purified by Biotage Flash™ chromatography, eluent: 1:7 EtOAc-hexanes, to afford 3,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamide as a white solid (0.150 g, 29.6%). Mass Spectrum (+ESI): 422 [M+H]+.

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 2N HCl (slow addition)
  3. additiondiluted with Et2O (40 mL)
  4. washThe organic layer was 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 (0.49 g)
  9. customThe crude product was purified by Biotage Flash™ chromatography, eluent

출처 및 근거

ORD 기록
ord-006a04f27819405f82941c8514e1c12c
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550629B2

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