Sodium borohydride → HCID 19385624, compound

HRID 1492586Notes

Reaction equation

HRID 1492586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH:20]=[O:21])[O:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH2:20][OH:21])[O:5][CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19385636HCID 19385636, compound

Product 1

HCID 19385624HCID 19385624, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 1.49 g (4.90 mmol) of the product of Step A dissolved in 20 mL of methanol was treated with 0.093 g (2.46 mmol) of sodium borohydride at room temperature. After 5 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was separated. The product was washed with water, brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 25% ethyl acetate/hexane to afford 1.380 g (92%) of the title compound.

Workup

  1. customAfter 5 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. customthe organic layer was separated
  3. washThe product was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6de56d6743224f99bb5ac962b7979cc3
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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