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

HRID 471460ノート

反応式

HRID 471460 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5c2d5c7caba04d2c8224c5ad9afedb85
出典データセット
uspto-grants-2014_01
特許番号
US08633182B2

反応ノート

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