Formic Acid → (S)-4-bromo-5-trifluoromethyl-indan-1-ol

HRID 471460노트

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HRID 471460 반응식
C(N(CC)CC)C.C(O)=O.[Br:11][C:12]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C:16]2=[O:25].O>ClCCl>[Br:11][C:12]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C@@H:16]2[OH:25]

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 867007731H-Inden-1-one, 4-bromo-2,3-dihydro-5-(trifluoromethyl)-

생성물 1

HCID 86700775(S)-4-bromo-5-trifluoromethyl-indan-1-ol수율 94.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Triethylamine (3.16 mL, 22.5 mmol) is dissolved in dichloromethane (40 mL) and cooled to 0° C. then formic acid (1.0 mL, 26.46 mmol) is added dropwise with cooling. After 20 minutes stirring 4-Bromo-5-trifluoromethyl-indan-1-one (2.1 g, 7.53 mmol) is added followed by Chloro([(1S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido)-(mesitylene)ruthenium(II) complex (220 mg, 0.35 mmol) and the mixture is stirred overnight under argon at room temperature. Water is added, the mixture shaken and the phases separated. The organic phase is dried and concentrated under vacuum. The residue is purified by flash chromatography (0-15% ethyl acetate in cyclohexane) to give the title compound (yield 2.0 g).

후처리

  1. temperaturewith cooling
  2. additionis added
  3. stirringthe mixture shaken
  4. customthe phases separated
  5. customThe organic phase is dried
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by flash chromatography (0-15% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-5c2d5c7caba04d2c8224c5ad9afedb85
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633182B2

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