Acetic Acid → HCID 25131531, compound

HRID 2076942Notes

Reaction equation

HRID 2076942 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][CH2:12][C@H:11]1[C:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:21][N:20]([CH2:33][C:34]([F:37])([F:36])[F:35])[N:19]=1)C1C=CC=CC=1.C(O)(=O)C>[OH-].[OH-].[Pd+2].C(OCC)(=O)C>[F:17][C:14]1([F:16])[CH2:15][C@@H:10]([CH2:9][OH:8])[C@H:11]([C:18]2[C:22]([C:23]3[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:27][CH:28]=3)=[CH:21][N:20]([CH2:33][C:34]([F:37])([F:36])[F:35])[N:19]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 25131882HCID 25131882, compound

Product 1

HCID 25131531HCID 25131531, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-{(1R,2R)-2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole (2.15 g, 3.97 mmol) and Pearlman's catalyst (1.0 g) were stirred together in ethyl acetate (50 mL) containing acetic acid (5 mL) under an atmosphere of hydrogen at rt for 20 h. The reaction mixture was then filtered through a Celite® pad and the filtrate was washed with saturated aqueous solutions of NaHCO3 and NaCl before drying over Na2SO4. Solvent removal in vacuo yielded {(1R,2R)-5,5-difluoro-2-[4-[4-(methylsulfonyl)phenyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]cyclohexyl}methanol as a faint-yellow, thick syrup. 1H NMR (400 MHz, acetone d6) δ 8.06 (1H, s), 7.96 (2H, d, J= 8.4 Hz), 7.79 (2H, d, J= 8.4 Hz), 5.08 (2H, q, J=8.8 Hz), 3.70 (1H, m), 3.47 (1H, m), 3.36 (1H, m), 3.16 (3H, s), 3.09 (1H, m), 2.38 (1H, m), 2.25 (1H, m), 2.15-1.30 (5H, m).

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite® pad
  2. washthe filtrate was washed with saturated aqueous solutions of NaHCO3 and NaCl
  3. dry with materialbefore drying over Na2SO4
  4. customSolvent removal in vacuo

Sources & evidence

ORD record
ord-767c835d09a244539e9b3c735699bd27
Source dataset
uspto-grants-2011_04
Patent number
US07928091B2

Reaction notes

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