Sodium Hydroxide → [2-(4-Chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acid

HRID 889386Notes

Reaction equation

HRID 889386 reaction equation
C([O:3][C:4](=[O:29])[CH:5]([C:12]1[N:13]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:14]=[C:15]2[CH2:21][CH2:20][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:28][C:25]1[CH:24]=[CH:23][C:22]([N:13]2[C:12]([CH:5]([CH:6]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]3)[C:4]([OH:29])=[O:3])=[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:15]3=[N:14]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67387348[2-(4-Chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester

Product 1

HCID 67387113[2-(4-Chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [2-(4-chloro-phenyl)-2,4,5,6,7,8-hexahydro-cycloheptapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester (337 mg, 812 umol) in MeOH (19 ml) and 4 N aqueous NaOH (3.05 ml, 12.2 umol) was heated for 14 h under reflux conditions. The solvent was removed under reduced pressure, ice water/2 N aqueous HCl solution/iPrOAc 1/1/2 was added and the layers were separated. The aqueous layer was extracted one more time 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 (284 mg, 734 umol; 90%) as off-white solid which was sufficiently pure to be used in the next step. MS: m/e=387.2 [M+H

Workup

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

Sources & evidence

ORD record
ord-26a0528c6b0649918c00188653e0ccac
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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