HCID 86702733, compound → HCID 86702734, compound

HRID 511744Notes

Reaction equation

HRID 511744 reaction equation
C([O:8][C:9]1[CH:16]2[CH:12]([CH2:13][CH:14]([CH:17]=[O:18])[CH2:15]2)[C:11](=[O:19])[C:10]=1[C:20]1[C:25]([CH2:26][CH3:27])=[CH:24][C:23]([CH3:28])=[CH:22][C:21]=1[CH2:29][CH3:30])C1C=CC=CC=1>[Pd].CO>[CH2:29]([C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([CH2:26][CH3:27])[C:20]=1[CH:10]1[C:11](=[O:19])[CH:12]2[CH:16]([CH2:15][CH:14]([CH:17]=[O:18])[CH2:13]2)[C:9]1=[O:8])[CH3:30]

Participants

4

Reactant 1

HCID 86702733HCID 86702733, compound

Product 1

HCID 86702734HCID 86702734, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

20 mg of palladium on activated carbon (10%) are added to 1.10 g (2.72 mmol) of 6-(benzyloxy)-5-(2,6-diethyl-4-methylphenyl)-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehyde in 20 ml of methanol, and the mixture is hydrogenated (15 bar, room temperature) for 20 h. The filtration and concentration on a rotary evaporator give 0.82 g (97%) of the title compound (I-a-3, isomer ratio according to 1H-NMR 4:1).

Workup

  1. custom(15 bar, room temperature)
  2. customfor 20 h
  3. filtrationThe filtration and concentration
  4. customon a rotary evaporator

Sources & evidence

ORD record
ord-716b6720c80044828fe7f82ac717b5c4
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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