Ethanol → Octahydro-1H-inden-4-ol

HRID 1858994Notes

Reaction equation

HRID 1858994 reaction equation
C[C:2]12[CH2:10][CH2:9][CH2:8][CH:7]1[CH2:6][CH2:5][CH2:4][CH2:3]2.C([OH:13])C>[Pd]>[CH2:8]1[CH:7]2[CH:2]([CH:3]([OH:13])[CH2:4][CH2:5][CH2:6]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 702EthanolHCID 12701552HCID 12701552, compound

Product 1

HCID 228140Octahydro-1H-inden-4-olYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Typically, the compound of formula VI, (1R,3aR,4S,7aR)-4-Hydroxy-1-[(S)-3-[2-(carboxylic acid ethyl ester)-phenyl-1-methyl-propynyl]-7a-methyl-octahydro-indene (218 mg; 0.615 mmol) was dissolved in dry ethanol (12 ml). Palladium on carbon (10%; 55 mg) was added and the reaction was put under hydrogen at one atmosphere for 12 hours at room temperature. The catalyst was filtered off and the solvent was evaporated. The compound of formula VI of the above Example 1E, the [1R,3aR,4S,7aR]-7a-Methyl-1-[(S)-1-methyl-3-[2-(carboxylic acid ethyl ester)-phenyl-propenyl]-octahydro-inden-4-ol (226 mg; yield: 100%) was obtained as a yellowish oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6fc63fe167b5497b8b6c5fe900d8cd07
Source dataset
uspto-grants-2000_11
Patent number
US06153605

Reaction notes

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