HCID 57067109, compound → HCID 86747421, compound

HRID 327316Notes

Reaction equation

HRID 327316 reaction equation
C(O[CH2:5][C:6]1[C@H:7]2[CH2:20][CH2:19][C@H:18]([CH3:21])[C@H:8]2[C@H:9]([O:12][CH:13]([O:15][CH2:16][CH3:17])[CH3:14])[O:10][CH:11]=1)(=O)C.[H][H]>C(OCC)(=O)C.N1C=CC=CC=1.[C].[Pd]>[CH2:16]([O:15][CH:13]([O:12][C@H:9]1[C@@H:8]2[C@@H:18]([CH3:21])[CH2:19][CH2:20][C@@H:7]2[C:6]([CH3:5])=[CH:11][O:10]1)[CH3:14])[CH3:17]

Participants

6

Reactant 2

HCID 57067109HCID 57067109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86747421HCID 86747421, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of this colorless oily substance, i.e., (1S, 4aS, 7S, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran, was dissolved in a mixed solvent of 100 ml of ethyl acetate and 3 ml of pyridine, and after 150 mg of 10% palladium carbon was added, the reaction mixture was stirred at room temperature for 20 hours in a hydrogen atmosphere of 1 atm. After the catalyst was filtered by celite, extraction was carried out by adding 100 ml of ethyl acetate to the reaction mixture solution. The organic layer was washed with 100 ml of 2N hydrochloric acid solution and saturated sodium chloride solution, and was then dried by magnesium sulfate. After filtration, the solvent was distilled off under a reduced pressure, and a colorless oily substance was obtained (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethylcyclopenta[c]pyran.

Workup

  1. filtrationAfter the catalyst was filtered by celite, extraction
  2. additionby adding 100 ml of ethyl acetate to the reaction mixture solution
  3. washThe organic layer was washed with 100 ml of 2N hydrochloric acid solution and saturated sodium chloride solution
  4. dry with materialwas then dried by magnesium sulfate
  5. filtrationAfter filtration
  6. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-0a5eab882dd045fdb1b240d04da7a0ec
Source dataset
uspto-grants-1993_12
Patent number
US05272172

Reaction notes

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