Chloroform → (1R,5S,6R,7R)-3,3-Ethylenedioxy-7-hydroxy-6-ethoxycarbonylbicyclo[3.3.0]octane

HRID 476554Notes

Reaction equation

HRID 476554 reaction equation
[CH2:1]1[CH2:18][O:17][C:3]2([CH2:10][C@H:9]3[C@H:5]([CH2:6][C:7](=[O:16])[CH:8]3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4]2)[O:2]1.C(Cl)(Cl)Cl.[BH4-].[Na+]>C(O)C>[CH2:18]1[CH2:1][O:2][C:3]2([CH2:10][C@H:9]3[C@H:5]([CH2:6][C@@H:7]([OH:16])[C@@H:8]3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4]2)[O:17]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 14061412HCID 14061412, compound

Product 1

HCID 14061416(1R,5S,6R,7R)-3,3-Ethylenedioxy-7-hydroxy-6-ethoxycarbonylbicyclo[3.3.0]octaneYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2.09 g of (1S,5R)-7,7-ethylenedioxy-2-ethoxycarbonylbicyclo[3.3.0]octan-3-one (I)' having [α]D21 +23.9° (c=2.55, CHCl3) in 21 ml of ethanol was added at -40° C. over 30 minutes 0.17 g of sodium borohydride. The mixture was stirred for 1 hour. After removal of ethanol in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (eluting solution: 20-50% (v/v) diethyl ether/n-hexane) to obtain 1.60 g of the oily title compound.

Workup

  1. customAfter removal of ethanol in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (eluting solution: 20-50% (v/v) diethyl ether/n-hexane)

Sources & evidence

ORD record
ord-5211463d193e4240b6483af5eff561cd
Source dataset
uspto-grants-1989_12
Patent number
US04885246

Reaction notes

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