HCID 131718285, compound → HCID 131718286, compound

HRID 2210659Notes

Reaction equation

HRID 2210659 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 131718285HCID 131718285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718286HCID 131718286, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1S, 4aS, 7R, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[ c]pyran (65 mg, 0.00024 mol) obtained in Example 26 was dissolved in 3 mι of ethyl acetate, and 0.05 mι of pyridine and 10% palladium carbon (3 mg) were added. The reaction mixture was stirred for 24 hours in a hydrogen gas atmosphere of 1 atm. After the catalyst was removed by celite filtration, concentration was effected. The residual matter was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=8:2 eluent was distilled off. A colorless oily substance was thus obtained, i.e., (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethylcyclopenta[c]pyran (43 mg, yield=82%). This (1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethylcyclopenta[c]pyran had the following physicochemical properties:

Workup

  1. additionwere added
  2. customAfter the catalyst was removed by celite filtration, concentration
  3. customThe residual matter was purified by chromatography
  4. customthe solvent of the fraction obtained from hexane
  5. distillationether=8:2 eluent was distilled off
  6. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-365a7ef0ea5e4b9fbf69ce9ae53be366
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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