Ethanol → HCID 131735772, compound

HRID 2202730Notes

Reaction equation

HRID 2202730 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]([C:17]([F:20])([F:19])[F:18])=[C:15]([C:21]([O:23]CC3C=CC=CC=3)=[O:22])[CH:14]=[N:13]2)[CH2:8][C@@H:7]1[CH3:31])=[O:5])[CH3:2].[CH2:32]([O:34][C:35]([C@@H:37]1[CH2:42][CH2:41][C@@H:40]([N:43]2[C:47]([C:48]([F:51])([F:50])[F:49])=[C:46]([C:52]([O:54]CC3C=CC=CC=3)=[O:53])[CH:45]=[N:44]2)[CH2:39][C@H:38]1[CH3:62])=[O:36])[CH3:33].CCO>[Pd].CCOC(C)=O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]([C:17]([F:18])([F:19])[F:20])=[C:15]([C:21]([OH:23])=[O:22])[CH:14]=[N:13]2)[CH2:8][C@@H:7]1[CH3:31])=[O:5])[CH3:2].[CH2:32]([O:34][C:35]([C@@H:37]1[CH2:42][CH2:41][C@@H:40]([N:43]2[C:47]([C:48]([F:49])([F:50])[F:51])=[C:46]([C:52]([OH:54])=[O:53])[CH:45]=[N:44]2)[CH2:39][C@H:38]1[CH3:62])=[O:36])[CH3:33]

Participants

5

Reactant 2

HCID 702EthanolHCID 131735773HCID 131735773, compound

Product 1

HCID 131735772HCID 131735772, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

A pressurized vial was charged with palladium 10 wt. % on activated carbon (0.103 g, 0.097 mmol) while under a stream of nitrogen gas. Then a solution of benzyl 1-((1R,3R,4R)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate compound with benzyl 1-((1S,3S,4S)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (1:1) (D43-3) (0.4258 g, 0.971 mmol) in a 1:1 mixture of EtOH (2.428 ml)/EtOAc (2.428 ml) was added into the vial. The reaction atmosphere was purged with hydrogen gas (3 times). The reaction was stirred vigorously under hydrogenation (33 psi) at 21° C. After 3 h, LCMS (ESI) showed that the reaction was complete. The reaction mixture was purged with nitrogen gas for 30 min. The mixture was filtered through a pad of celite and the filter cake was rinsed with EtOAc. The filtrate was concentrated in vacuo to give 1-((1R,3R,4R)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid compound with 1-((1S,3S,4S)-4-(ethoxycarbonyl)-3-methylcyclohexyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (1:1) (D43) (0.3224 g, 0.926 mmol, 95% yield) as light-yellow solid:

Workup

  1. additionwas added into the vial
  2. customThe reaction atmosphere
  3. customwas purged with hydrogen gas (3 times)
  4. customThe reaction mixture was purged with nitrogen gas for 30 min
  5. filtrationThe mixture was filtered through a pad of celite
  6. washthe filter cake was rinsed with EtOAc
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee57499161474571b85d9f36c36bdb29
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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