HCID 131718290, compound → HCID 131718289, compound

HRID 1492682Notes

Reaction equation

HRID 1492682 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 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

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 ml 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. customThe catalyst was removed by celite filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residual substance was purified by chromatography
  4. customthe solvent of the fraction obtained from hexane
  5. distillationether=2:8 eluent was distilled
  6. customa colorless oily substance was obtained

Sources & evidence

ORD record
ord-36e59b63519847ce9fbf3386e306dd7f
Source dataset
uspto-grants-1994_12
Patent number
US05374653

Reaction notes

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