HCID 6325197, compound → HCID 10867925, compound

HRID 1384994Notes

Reaction equation

HRID 1384994 reaction equation
[OH:1][CH:2]1[C@@H:7]2[C:8]([CH2:11][OH:12])=[CH:9][CH2:10][C@@H:6]2[C:5]([C:13]([O:15][CH3:16])=[O:14])=[CH:4][O:3]1>C(Cl)Cl>[CH:11]([C:8]1[C@H:7]2[CH:2]([OH:1])[O:3][CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C@H:6]2[CH2:10][CH:9]=1)=[O:12]

Participants

3

Reactant 1

HCID 6325197HCID 6325197, compound

Product 1

HCID 10867925HCID 10867925, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (44.2 mmol) of methyl(4aS,7aS)-1-hydroxy-7-hydroxymethyl-1,4a,5,7a-tetra hydrocyclopenta[c]pyrane-4-carboxylate was dissolved with 600 ml of methylene chloride, and 19.06 g (88.4 mmol) of pyridiniumchlorocromate was added, and stirred for 2 hours. After filtering the reaction mixture, the filtered solution was concentrated and purified by using column chromatography (hexane/ethylacetate=3/1, v/v), and 8.78 g of methyl(4aS,7aS)-7-formyl-1-hydroxy-1,4a,5,7a-tetra hydrocyclopenta[c]pyrane-4-carboxylate was obtained (yield: 89%).

Workup

  1. additionwas added
  2. filtrationAfter filtering the reaction mixture
  3. concentrationthe filtered solution was concentrated
  4. custompurified

Sources & evidence

ORD record
ord-a462256455e34ce2a7e6da43347ddcab
Source dataset
uspto-grants-2001_07
Patent number
US06262083B1

Reaction notes

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