HCID 11096141, compound → HCID 86601630, compound

HRID 1268710Notes

Reaction equation

HRID 1268710 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([C@H:10]([OH:13])CO)[C@H:4]2[O:3]1>C(OCC)(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[CH2:7][S:8][C@H:9]([CH:10]=[O:13])[C@H:4]2[O:3]1

Participants

4

Reactant 1

HCID 11096141HCID 11096141, compound

Product 1

HCID 86601630HCID 86601630, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 178418268HCID 178418268, compoundSolvent

Procedure

2.5 g (11.2 mmol) of (1R)-1-((3aS,4R,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol from the aforementioned Experimental Example 5 were dissolved in ethyl acetate to which lead tetraacetate were added at 0° C., and the reaction mixture was stirred for 10 min. The reaction mixture was filtered. Ethyl acetate was added to the filtrate, which was washed with saturated sodium bicarbonate, dried, and filtered. The filtrate was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography using the eluant (hexane:ethyl acetate=5:1) to obtain 2.1 g (yield: 98%) of (3aS,4S,6aR)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole-4–Carbaldehyde as an oil.

Workup

  1. additionwere added at 0° C.
  2. filtrationThe reaction mixture was filtered
  3. additionEthyl acetate was added to the filtrate, which
  4. washwas washed with saturated sodium bicarbonate
  5. customdried
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5104219b74d34fef96b7f51a3c42687c
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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