Triacetoxyperiodinane → 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanone

HRID 60712Notes

Reaction equation

HRID 60712 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]2[O:7][C@H:8]([C@@H:10]([OH:14])[CH2:11][O:12][CH3:13])[CH2:9][C@H:4]2[O:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:15])[O:6][C@H:5]2[O:7][C@H:8]([C:10](=[O:14])[CH2:11][O:12][CH3:13])[CH2:9][C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 121396399HCID 121396399, compound2×

Product 1

HCID 1213963641-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanoneYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanol (compound 21b, 1.62 g, 7.4 mmol) in DCM (50 mL) was added Dess-Martine periodinane (4.7 g, 11 mmol) with stirring. After being stirred at room temperature for 2 hours, the resulting solution was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 1.4 g of 1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-methoxy-ethanone (compound 21c) as a colorless oil. MS obsd. (ESI+) [(M+NH4)+]: 234.

Workup

  1. stirringAfter being stirred at room temperature for 2 hours
  2. filtrationthe resulting solution was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-173df030b0e147b892e94b8d1d652715
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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