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

HRID 2170928ノート

反応式

HRID 2170928 の反応式
C(O)=O.[Br:4][C:5]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:18]>C(Cl)Cl.Cl>[Br:4][C:5]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C@@H:9]2[OH:18]

参加物

5

反応物 2

HCID 284Formic AcidHCID 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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

Under argon atmosphere: 1.89 ml (13.6 mmol) TEA are dissolved in 15.0 ml DCM. Under ice cooling 0.59 ml (15.8 mmol) of formic acid are added. At r.t. 100 mg (3.58 mmol) of 4-bromo-5-trifluoromethyl-indan-1-one and 49.6 mg (0.07 mmol) of chloro{[(1S,2S)-(−)-2-amino-1,2-diphenylethyl](4-toluenesulfonyl)amido}-(mesitylene)-ruthenium(II) are added. The reaction mixture is stirred at r.t. for 48 h. The mixture is diluted with 20 ml 1N aq. HCl. The phases are separated. The aq. phase is washed with DCM. The combined organic layers are washed with brine, dried and the solvent is evaporated. The residue is chromatographed on silica gel (CH/EtOAc=75/25→50/50) to give the title compound. Yield: 1.03 g; LC (method 1): tR=1.01 min.

後処理

  1. customAt r.t
  2. customThe phases are separated
  3. washThe aq. phase is washed with DCM
  4. washThe combined organic layers are washed with brine
  5. customdried
  6. customthe solvent is evaporated
  7. customThe residue is chromatographed on silica gel (CH/EtOAc=75/25→50/50)

出典と根拠

ORDレコード
ord-30993f7b6a6f47c89bf069d7e03802e8
出典データセット
uspto-grants-2015_06
特許番号
US09051289B2

反応ノート

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