HCID 69949538, compound → 4-CarboxyMethyl-cyclohexanecarboxylic acid ethyl ester

HRID 2298965Notes

Reaction equation

HRID 2298965 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH2:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 69949538HCID 69949538, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 158961924-CarboxyMethyl-cyclohexanecarboxylic acid ethyl esterYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of diester (B) (12.5 g, 46.3 mmol) and 10% palladium on activated carbon (5 g) in absolute ethanol (200 mL) was exposed to a hydrogen atmosphere (at balloon pressure) and stirred vigorously for 1 h. After removal of catalyst by filtration and concentration, the resultant colorless oil was dissolved in methylene chloride (150 mL) and TFA (75 mL) and stirred for 15 min. All volatiles were removed by rotary evaporation and the resultant colorless oil placed under high vacuum to give (C) 4-carboxymethyl-cyclohexanecarboxylic acid ethyl ester (9.9 g, 99%) as a white solid. Data for cis/trans mixture: 1H NMR (400 MHz, CD3OD) δ4.13 (2q, 4 H), 2.58 (m, 1H), 2.30-2.20 (m, 1 H), 2.20 (2d, 4 H), 2.05-1.80 (m, 7 H), 1.80-1.55 (m, 5 H), 1.50-1.38 (m, 3 H), 1.32-1.25 (m, 1 H), 1.25 (2t, 6 H), 1.10-1.00 (m, 2 H); mass spectrum m/z 215 [(M+H)+; calcd for C11H19O4: 215].

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration and concentration
  3. dissolutionthe resultant colorless oil was dissolved in methylene chloride (150 mL)
  4. stirringTFA (75 mL) and stirred for 15 min
  5. customAll volatiles were removed by rotary evaporation

Sources & evidence

ORD record
ord-4eae9c3e84fc40fb8eb38ab3fffa9aa5
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

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