Sodium borohydride → HCID 68458743, compound

HRID 2358748Notes

Reaction equation

HRID 2358748 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[CH:10]=[CH:11][CH:12]=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]=[C:9]([CH:13]([OH:15])[CH3:14])[CH:10]=[CH:11][CH:12]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68461162HCID 68461162, compound

Product 1

HCID 68458743HCID 68458743, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the product from Example 170a (1.8 g, 6.2 mmol) in ethanol (50 mL) was added sodium borohydride (0.32 g, 8.64 mmol) portion wise. The reaction was stirred at room temperature for 16 h. The excess sodium borohydride was destroyed by 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. The crude residue was purified by silica gel chromatography eluting with (hexanes/ethyl acetate/methanol (75:15:5) to give the desired product (0.98 g, 54%).

Workup

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

Sources & evidence

ORD record
ord-bda277b4ba1e4db29a9544b93db600cf
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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