Pyridine → HCID 86747421, compound

HRID 327304Notes

Reaction equation

HRID 327304 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.N1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[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 3

HCID 1049PyridineHCID 57067109HCID 57067109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86747421HCID 86747421, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(1S, 4aS, 7S, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran (40.0 g, 0.135 mol) obtained in Example 6 was dissolved in 1,000 ml of ethyl acetate. After 20 ml of pyridine was added, 10% palladium carbon (1.2 g) was suspended in the reaction solution, and this solution was stirred for 48 hours in a hydrogen gas atmosphere of 1 atm. After the catalyst was removed by celite filtration, 1,000 ml of ethyl acetate was added, and this organic layer was washed with 2N hydrochloric acid solution (1,000 ml) and saturated sodium chloride solution (1,000 ml). The organic layer was dried by magnesium sulfate, and was filtered, and then concentrated under a reduced pressure. 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, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethyl-cyclopenta[c]pyran (29.5 g, yield=93.1%). This (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethylcyclopenta[c]pyran had the following physicochemical properties:

Workup

  1. customAfter the catalyst was removed by celite filtration, 1,000 ml of ethyl acetate
  2. additionwas added
  3. washthis organic layer was washed with 2N hydrochloric acid solution (1,000 ml) and saturated sodium chloride solution (1,000 ml)
  4. dry with materialThe organic layer was dried by magnesium sulfate
  5. filtrationwas filtered
  6. concentrationconcentrated under a reduced pressure
  7. customThe residual matter was purified by chromatography
  8. customthe solvent of the fraction obtained from hexane
  9. distillationether=8:2 eluent was distilled off
  10. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-46b0582ddb334ec3a1ab1cf01cf5576c
Source dataset
uspto-grants-1993_12
Patent number
US05272172

Reaction notes

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