HCID 58070838, compound → HCID 58070830, compound

HRID 1193034Notes

Reaction equation

HRID 1193034 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:24](=[O:25])[CH:23]3[CH:18]([CH:19]4[CH2:27][CH2:26][CH:22]3[CH2:21][CH2:20]4)[C:17]=2[O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:11]([CH3:35])[CH:10]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:24](=[O:25])[CH:23]3[CH:18]([CH:19]4[CH2:27][CH2:26][CH:22]3[CH2:21][CH2:20]4)[C:17]=2[O:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])=[C:11]([CH3:35])[CH:10]=1

Participants

5

Reactant 2

HCID 58070838HCID 58070838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58070830HCID 58070830, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethylpropionic acid 2-(4-benzyloxy-2,6-dimethylphenyl)-3-oxo-3a,4,5,6,7,7a-hexahydro-3H-4,7-ethanoinden-1-yl ester (2.8 g, 0.006 mol) in methanol (250 ml) is added 10% palladium on carbon (0.50 g), and the suspension is stirred under a 4 bar hydrogen pressure for 5 hours. The reaction mixture is then filtered through a pad of diatomaceous earth and the filtrate is evaporated under reduced pressure. The crude product is triturated with diethyl ether to afford 2,2-dimethylpropionic acid 2-(4-hydroxy-2,6-dimethylphenyl)-3-oxo-3a,4,5,6,7,7a-hexahydro-3H-4,7-ethanoinden-1-yl ester.

Workup

  1. filtrationThe reaction mixture is then filtered through a pad of diatomaceous earth
  2. customthe filtrate is evaporated under reduced pressure
  3. customThe crude product is triturated with diethyl ether

Sources & evidence

ORD record
ord-0dd49e8a282b48c79c76a31d4151451e
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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