Sodium borohydride → HCID 21476897, compound

HRID 2293582Notes

Reaction equation

HRID 2293582 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 21476898HCID 21476898, compound

Product 1

HCID 21476897HCID 21476897, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.609 g (2.96 mmol) of the product of Step C dissolved in 10 mL of methanol was added 0.056 g (1.48 mmol) of sodium borohydride in small portions as the reaction mixture was stirred at room temperature under a nitrogen atmosphere. After stirring for 30 minutes the excess sodium borohydride was quenched by addition of 10% aqueous NaHSO4. The methanol was removed in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then purified on a silica gel flash chromatography column eluted with 20% EtOAc-hexane; evaporation of the purified fractions and drying in vacuo afforded 0.408 g (66%) of the title compound.

Workup

  1. customwas quenched by addition of 10% aqueous NaHSO4
  2. customThe methanol was removed in vacuo
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified on a silica gel flash chromatography column
  9. washeluted with 20% EtOAc-hexane
  10. customevaporation of the purified fractions
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-99d17b48bd9b4aeba03a9d1d2795067d
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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