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

HRID 2170928Notes

Reaction equation

HRID 2170928 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-30993f7b6a6f47c89bf069d7e03802e8
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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