Tetrahydrofuran → HCID 57052900, compound

HRID 1265321Notes

Reaction equation

HRID 1265321 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 Celite®, and filtrate and evaporated to give (1S,2R)-2-(3,5-difluorophenyl-methyl)cyclohexanecarboxylic acid, as a white solid (0.9 g, 95%).

Workup

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

Sources & evidence

ORD record
ord-2b064f970791449d916f6be698267c68
Source dataset
uspto-grants-2003_04
Patent number
US06545160B2

Reaction notes

Loading…