HCID 131718290, compound → HCID 131718289, compound

HRID 2210666Notes

Reaction equation

HRID 2210666 reaction equation
C(O[C@H:5]1[C@H:10]2[C:11]([CH2:14]OC(=O)C)=[CH:12][CH2:13][C@@H:9]2[C:8]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][O:6]1)(=O)C.[H][H]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:14][CH:11]1[C@H:10]2[CH2:5][O:6][CH:7]=[C:8]([C:19]([O:21][CH3:22])=[O:20])[C@H:9]2[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 131718290HCID 131718290, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718289HCID 131718289, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 9942167Palladium hydroxideSolvent

Procedure

After methyl (1S, 4aS, 7aR)-1-acetoxy-7-(acetoxymethyl)-1, 4a, 5, 7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (100 mg, 0.0003 mol) obtained in Example 21 was dissolved in 5 mι of ethyl acetate, 20% Pd(OH)2 --C (5 mg) was added to the solution, and the reaction mixture was stirred for 24 hours in a hydrogen gas atmosphere of 1 atm. The catalyst was removed by celite filtration and the filtrate was concentrated. The residual substance was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=2:8 eluent was distilled, and a colorless oily substance was obtained, i.e., methyl (4aS, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran-4-carboxylate (48 mg, yield=30.4%). This methyl (4aS, 7aR)-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran-4-carboxylate had the following physicochemical properties.

Workup

  1. additionC (5 mg) was added to the solution
  2. customThe catalyst was removed by celite filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residual substance was purified by chromatography
  5. customthe solvent of the fraction obtained from hexane
  6. distillationether=2:8 eluent was distilled
  7. customa colorless oily substance was obtained

Sources & evidence

ORD record
ord-09de26573d094670824f0476def1b914
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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