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

HRID 1987588ノート

反応式

HRID 1987588 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-006a04f27819405f82941c8514e1c12c
出典データセット
uspto-grants-2009_06
特許番号
US07550629B2

反応ノート

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