Ammonium formate → HCID 131718279, compound

HRID 327307Notes

Reaction equation

HRID 327307 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C:3]([O:5][C@H:6]1[C@@H:11]2[C:12]([CH2:15]OC(=O)C(C)(C)C)=[CH:13][CH2:14][C@@H:10]2[C:9]([C:23]([O:25][CH3:26])=[O:24])=[CH:8][O:7]1)=[O:4].C([O-])=O.[NH4+]>O1CCCC1.[C].[Pd]>[CH3:15][C:12]1[C@H:11]2[C@H:6]([O:5][C:3](=[O:4])[C:2]([CH3:28])([CH3:27])[CH3:1])[O:7][CH:8]=[C:9]([C:23]([O:25][CH3:26])=[O:24])[C@H:10]2[CH2:14][CH:13]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 131718280HCID 131718280, compound

Product 1

HCID 131718279HCID 131718279, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Methyl (1S, 4aS, 7aS)-1, 4a, 5, 7a-tetrahydro-1-trimethylacetoxy-7-(trimethylacetoxymethyl)cyclopenta[c]-pyran-4-carboxylate (200 mg, 0.00051 mol) obtained in Example 14 was dissolved in 15 ml of tetrahydrofuran, and 10% palladium carbon (10 mg) was suspended. After ammonium formate (320 mg, 0.0046 mol) was added, the reaction mixture was refluxed at 80° C. Twelve hours later, celite filtration was carried out, and 50 ml of ethyl acetate was added to the filtrate. After this organic layer was washed with saturated sodium chloride solution (30 ml), it was dried by adding magnesium sulfate, 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 concentrated. A colorless oily substance was thus obtained, i.e., methyl (1S, 4aS, 7aS)-1, 4a, 5, 7a-tetrahydro-7-methyl-1-trimethylacetoxycyclopenta[c]pyran-4-carboxylate (114.5 mg, yield=72.8%). This methyl (1S, 4aS, 7aS)-1, 4a, 5, 7a-tetrahydro-7-methyl-1-trimethylacetoxycyclopenta[c]pyran-4-carboxylate had the following physicochemical properties:

Workup

  1. filtrationTwelve hours later, celite filtration
  2. addition50 ml of ethyl acetate was added to the filtrate
  3. washAfter this organic layer was washed with saturated sodium chloride solution (30 ml), it
  4. customwas dried
  5. additionby adding magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under a reduced pressure
  8. customThe residual matter was purified by chromatography
  9. customthe solvent of the fraction obtained from hexane ether=8:2 eluent
  10. concentrationwas concentrated
  11. customA colorless oily substance was thus obtained

Sources & evidence

ORD record
ord-4738c96bfca640f38393ff79fc5677d0
Source dataset
uspto-grants-1993_12
Patent number
US05272172

Reaction notes

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