Sodium borohydride → HCID 43506274, compound

HRID 2358733Notes

Reaction equation

HRID 2358733 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][CH:12]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9212449HCID 9212449, compound

Product 1

HCID 43506274HCID 43506274, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 164a (0.7 g, 2.4 mmol) was added to ethanol (30 mL) and sodium borohydride (115 g, 3.11 mmol) was added portion wise. The reaction was stirred for 1 h and then the excess sodium borohydride was destroyed by drop wise addition of acetic acid. The reaction was poured onto ice/water and extracted with ethyl acetate. The organic phase washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (0.634 g, 90%).

Workup

  1. additionwas added portion wise
  2. customthe excess sodium borohydride was destroyed by drop wise addition of acetic acid
  3. additionThe reaction was poured onto ice/water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-220683b065a54016a27c44e9fc104b38
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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