Sodium borohydride → HCID 21700870, compound

HRID 1870790Notes

Reaction equation

HRID 1870790 reaction equation
[BH4-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[S:8]1(=[O:19])=[O:18]>C(O)C>[Cl:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][CH:11]([OH:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[S:8]1(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21700841HCID 21700841, compound

Product 1

HCID 21700870HCID 21700870, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

200 mg (5.29 mmol) of sodium borohydride was added in portions to a solution of 620 mg (2.27 mmol) of the Compound 5 in 20 ml of ethanol while stirring under cooling with ice. After stirring for 17 hours at room temperature, the reaction mixture was concentrated under vacuum. A 0.1 M phosphate buffer solution (pH 6.0) was added to the residue and the mixture was extracted with chloroform (three times). The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography using a 1:1 ethyl acetate-hexane solution as an eluent to obtain 567 mg (yield: 91%) of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring for 17 hours at room temperature
  3. concentrationthe reaction mixture was concentrated under vacuum
  4. additionA 0.1 M phosphate buffer solution (pH 6.0) was added to the residue
  5. extractionthe mixture was extracted with chloroform (three times)
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3756728614564dc48424522db0b493f2
Source dataset
uspto-grants-2000_08
Patent number
US06100265

Reaction notes

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