Sodium borohydride → HCID 19385715, compound

HRID 2399482Notes

Reaction equation

HRID 2399482 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:21]=[C:20]([CH2:22][OH:23])[CH:19]=[CH:18][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19385702HCID 19385702, compound

Product 1

HCID 19385715HCID 19385715, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 1.74 g (5.54 mmol) of the product of Step A dissolved in 22 mL of methanol was treated with 0.105 g (2.8 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 30% ethyl acetate/hexane to afford 1.15 g (66%) 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 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-67c546f034484bacb24de3d4d947942b
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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