Tetrahydrofuran → HCID 57052900, compound

HRID 2188334Notes

Reaction equation

HRID 2188334 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]([C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[C:17]([OH:19])=[O:18])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.O1CCCC1>[OH-].[OH-].[Pd+2].C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[C:17]([OH:19])=[O:18])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 40793565HCID 40793565, compound

Product 1

HCID 57052900HCID 57052900, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (1S, 2R)-2-(3,5-difluorophenylcarbonyl)cyclohexanecarboxylic acid (1 g, 3.7 mmol), 10% Pd(OH)2 on carbon (1 g), tetrahydrofuran (10 mL) and acetic acid (0.5 mL) was shaken under hydrogen atmosphere at 50 psi for 96 h. The reaction mixture was filtered through CeliteR, and filtrate and evaporated to give (1S, 2R)-2-(3,5-difluorophenylmethyl)cyclohexanecarboxylic acid, as a white solid (0.9 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered through CeliteR, and filtrate
  2. customevaporated

Sources & evidence

ORD record
ord-3ad25e0fd0d3490494fa38c1280ba9ba
Source dataset
uspto-grants-2002_06
Patent number
US06410781B1

Reaction notes

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