HCID 57278509, compound → HCID 86755121, compound

HRID 377089Notes

Reaction equation

HRID 377089 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C@H:12]2[CH2:24][C@H:23]3O[C@@:22]3(C)[C@@H:13]2[C@H:14]([O:17][C:18](=[O:21])[NH:19][CH3:20])[O:15][CH:16]=1)=[O:10])C1C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:8][C:9]([C:11]1[CH:12]2[CH2:24][CH2:23][CH2:22][CH:13]2[CH:14]([O:17][C:18](=[O:21])[NH:19][CH3:20])[O:15][CH:16]=1)=[O:10]

Participants

4

Reactant 1

HCID 57278509HCID 57278509, compound

Product 1

HCID 86755121HCID 86755121, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.35 g of (1S,4aS,6R,7S,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid benzylester described in Step 5 of Example 1 were dissolved in ethyl acetate followed by suspension of 60 mg of 5% palladium-carbon catalyst and stirring for 24 hours under hydrogen gas atmosphere at 1 atm. After filtering out the insoluble matter, the filtrate was concentrated. The residue was dissolved in methanol-ether followed by dropwise addition of 3.0 ml of trimethylsilyldiazomethane (2.0 M, hexane solution) and stirring for 30 minutes at room temperature. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ether eluate in the form of (1S,4aS,6R,7S,7aR)-6,7-epoxy-7-methyl-1-(methylcarbamoyloxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyrane-4-carboxylic acid methylester (720 mg, yield: 68%). The physicochemical properties of this compound are described in Table 12, Compound No. 57.

Workup

  1. filtrationAfter filtering out the insoluble matter
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in methanol-ether
  4. additionfollowed by dropwise addition of 3.0 ml of trimethylsilyldiazomethane (2.0 M, hexane solution)
  5. stirringstirring for 30 minutes at room temperature
  6. extractionThe reaction mixture was then extracted with ethyl acetate
  7. washAfter washing the organic phase with brine, it
  8. dry with materialwas dried over magnesium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure
  10. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8ac15be0cf714e9b8b0c6e51d96052f0
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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