Ethyl Acetate → 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cycloheptyl-ethanol

HRID 417141Notes

Reaction equation

HRID 417141 reaction equation
C([O:3][C:4](=O)[CH:5]([N:13]1[C:17]2[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:16]=2[N:15]=[C:14]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(OCC)(=O)C>O1CCCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:14]2[N:13]([CH:5]([CH:6]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[CH2:4][OH:3])[C:17]3[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:16]=3[N:15]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 66619224[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cycloheptyl-acetic acid ethyl ester

Product 1

HCID 666194822-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cycloheptyl-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.4 g (3.13 mmol) [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cycloheptyl-acetic acid ethyl ester in 20 ml dry tetrahydrofuran was added 0.125 g (3.29 mmol) lithium aluminum hydride at 0° C. The reaction mixture was stirred for 2 hours at room temperature and then poured on 100 ml 10% aqueous sodium-potassium-tartrate solution and 100 ml ethyl acetate. The aqueous layers were extracted again with 100 ml ethyl acetate. The organic layers were washed with 100 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (2:1). Colorless solid (74%). MS (TurboSpray): 405.3 [M+H].

Workup

  1. extractionThe aqueous layers were extracted again with 100 ml ethyl acetate
  2. washThe organic layers were washed with 100 ml brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of n-heptane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-6833508bba704ce792af2a7dfc840d46
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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