Pyridine → HCID 131718285, compound

HRID 2210658Notes

Reaction equation

HRID 2210658 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[C@@H:12]2[C@H:13]([CH3:16])[CH2:14][CH2:15][C@@H:11]2[C:10]([CH2:17][OH:18])=[CH:9][O:8]1)[CH3:5])[CH3:2].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(OCC)(=O)C>ClCCl>[C:25]([O:18][CH2:17][C:10]1[C@H:11]2[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@H:12]2[C@H:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[O:8][CH:9]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 131718283HCID 131718283, compound

Product 1

HCID 131718285HCID 131718285, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S, 4aS, 7R, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4-(hydroxymethyl)-7-methylcyclopenta[c]pyran (100 mg, 0.00039 mol) obtained in Example 25 was dissolved in 5 mι of dichloromethane, and 0.15 mι (0.0016 mol) of pyridine and 0.1 mι (0.0012 mol) of acetic anhydride were added. Furthermore, 5 mg of N, N-dimethylaminopyridine was added, the reaction mixture was stirred at room temperature for 5 hours. Then, the reaction mixture was poured into 30 mι of ethyl acetate, and the organic layer was washed with water (30 mι), 2N hydrochloric acid solution (30 mι), saturated sodium bicarbonate solution (30 mι) and saturated sodium chloride solution (30 mι), was dried by adding magnesium sulfate, was filtered, and then concentrated under a reduced pressure. The residual matter was purified by chromatography using silica gel, and the fraction obtained from hexane:ether=6:4 eluent was concentrated. A colorless oily substance was thus obtained, i.e., (1S, 4aS, 7R, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran (71 mg, yield=61.0%). This (1S, 4aS, 7R, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[ c]pyran had the following physicochemical properties:

Workup

  1. additionwere added
  2. washthe organic layer was washed with water (30 mι), 2N hydrochloric acid solution (30 mι), saturated sodium bicarbonate solution (30 mι) and saturated sodium chloride solution (30 mι)
  3. customwas dried
  4. additionby adding magnesium sulfate
  5. filtrationwas filtered
  6. concentrationconcentrated under a reduced pressure
  7. customThe residual matter was purified by chromatography
  8. customthe fraction obtained from hexane
  9. concentrationether=6:4 eluent was concentrated
  10. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-bff5cecc209f4f4a99601511c3429e87
Source dataset
uspto-grants-1995_10
Patent number
US05459160

Reaction notes

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