Sodium Hydroxide → [2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid

HRID 889375Notes

Reaction equation

HRID 889375 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([C:12]1[N:13]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:14]=[C:15]2[CH2:19][CH2:18][CH2:17][C:16]=12)[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[OH-].[Na+]>CO>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([N:13]2[C:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[C:4]([OH:27])=[O:3])=[C:16]3[CH2:17][CH2:18][CH2:19][C:15]3=[N:14]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67387258[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester

Product 1

HCID 67387271[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acidYield 61.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [2-(4-chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester (1 g, 2.6 mmol; example 1.3) in MeOH (56 ml) and 4 N aqueous NaOH (9.7 ml, 39 mmol) was stirred at ambient temperature for 14 h. The solvent was removed under reduced pressure, ice water/TBME 1/1 was added and the layers were separated. The aqueous layer was extracted one more time with TBME. The aqueous layer was acidified with 1 N aqueous HCl solution and 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 give the title compound (570 mg, 1.59 mmol; 61%) as yellow oil which was sufficiently pure to be used in the next step. MS: m/e=359.2 [M+H+].

Workup

  1. customThe solvent was removed under reduced pressure, ice water/TBME 1/1
  2. additionwas added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted one more time with TBME
  5. extractionextracted two times with iPrOAc
  6. washThe combined extracts were washed with ice water/brine 1/1
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration the solvent
  9. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-d1ead003f87c404e9e4c74e58088bae4
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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