Lithium Hydroxide → 4-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid

HRID 889374Notes

Reaction equation

HRID 889374 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11][CH2:12][CH:13]([C:20]2[N:21]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:22]=[C:23]3[CH2:27][CH2:26][CH2:25][C:24]=23)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:6]([CH3:35])[CH:5]=1.[OH-].[Li+]>C1COCC1.CO>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([N:21]2[C:20]([CH:13]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][O:11][C:7]3[C:8]([CH3:10])=[CH:9][C:4]([C:3]([OH:36])=[O:2])=[CH:5][C:6]=3[CH3:35])=[C:24]3[CH2:25][CH2:26][CH2:27][C:23]3=[N:22]2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 533902524-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl ester

Product 1

HCID 533775864-{2-[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acidYield 137%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{2-[2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-2-cyclohexyl-ethoxy}-3,5-dimethyl-benzoic acid methyl ester (19 mg, 37 umol; example 1.5) in THF (0.7 ml) and MeOH (0.3 ml) was a added a 1 N aqueous lithium hydroxide solution (450 ul, 450 umol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred for 14 h at ambient temperature and poured onto ice water/1 N aqueous HCl solution 1/1. The mixture was extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to obtain the title compound (25 mg; quant.) as colorless oil.

Workup

  1. additionpoured onto ice water/1 N aqueous HCl solution 1/1
  2. extractionThe mixture was extracted two times with iPrOAc
  3. washThe combined extracts were washed with ice water/brine 1/1
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-4c052b309a3a4e9ab6cf7ccdcd5242b9
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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