Pyridine → HCID 131718286, compound

HRID 327312Notes

Reaction equation

HRID 327312 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 131718285HCID 131718285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131718286HCID 131718286, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 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 ml of ethyl acetate, and 0.05 ml 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. customAfter the catalyst was removed by celite filtration, concentration
  2. customThe residual matter was purified by chromatography
  3. customthe solvent of the fraction obtained from hexane ether=8:2 eluent
  4. distillationwas distilled off A colorless oily substance
  5. customwas thus obtained

Sources & evidence

ORD record
ord-86e1cbfdb375416294a5cb31f578c035
Source dataset
uspto-grants-1993_12
Patent number
US05272172

Reaction notes

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