Sodium borohydride → (1S,3aS,5S,7aR)-1-acetoxymethyl-7a-methylperhydroinden-3a,5-diol

HRID 725184Notes

Reaction equation

HRID 725184 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@:14]2([CH3:15])[C@@:9]([OH:17])([CH2:10][C:11](=[O:16])[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:4][CH2:5][C@@H:6]1[C@:14]2([CH3:15])[C@@:9]([OH:17])([CH2:10][C@@H:11]([OH:16])[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22880912(1S,3aS,7aR)-1-acetoxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone

Product 1

HCID 57054118(1S,3aS,5S,7aR)-1-acetoxymethyl-7a-methylperhydroinden-3a,5-diolYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.00 g of (1S,3aS,7aR)-1-acetoxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone (see Prepn. 3) in 50 ml of methanol cooled at 0° C., 0.77 g of NaBH4 were added and the mixture was stirred for 1 hr. It was then diluted with 10 ml of 5% aqueous NaH2PO4.H2O, concentrated in vacuo and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) with n-hexane/chloroform/acetone 4:3:3 as the eluant to give 2.18 g of (1S,3aS,5S,7aR)-1-acetoxymethyl-7a-methylperhydroinden-3a,5-diol as a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by flash-chromatography (SiO2) with n-hexane/chloroform/acetone 4:3:3 as the eluant

Sources & evidence

ORD record
ord-2b8071db366f4eb699edd624b33f3e93
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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