Water → (3s,3ar,6as)-Hexahydrofuro[2,3-B]furan-3-Ol

HRID 984531Notes

Reaction equation

HRID 984531 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C@@H:11]2[O:12][CH2:13][CH2:14][C@H:10]2[C:9](=[O:15])[CH2:8]1.O.[OH-].[Na+]>C1COCC1>[O:7]1[C@@H:11]2[O:12][CH2:13][CH2:14][C@@H:10]2[C@H:9]([OH:15])[CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20767149(3aR,6aS)-hexahydrofuro[2,3-b]furan-3-onHCID 21226445Aluminium lithium hydride

Product 1

HCID 10374488(3s,3ar,6as)-Hexahydrofuro[2,3-B]furan-3-OlYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (15 mg) dispersed in THF (0.2 mL) was added dropwise a solution of (3aR,6aS)-hekahydrofuro[2,3-b]furan-3-on (64 mg) obtained in Example 28 in THF (0.5 mL) at 0° C. and the mixture was stirred for 1 hr. Water (0.1 mL), 15% aqueous sodium hydroxide solution (0.1 mL) and water (0.3 mL) were successively added to the reaction mixture every 30 min and the mixture was filtered and washed well with THF. The filtrate was dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated to give the title compound (57 mg, 88% ee) as an oil, which was an almost pure anti-form. The spectrum data were the same as those in Example 27.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed well with THF
  3. dry with materialThe filtrate was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54e683b5440a47bca6db4ff96dc41dbf
Source dataset
uspto-grants-2005_03
Patent number
US06867321B2

Reaction notes

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