Sodium borohydride → HCID 67236887, compound

HRID 2364868Notes

Reaction equation

HRID 2364868 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:23])[CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:23])[CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=2)[OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67236410HCID 67236410, compound

Product 1

HCID 67236887HCID 67236887, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 191A (4.62 g, 11.65 mmole) was mixed with EtOH (100 mL) and the resulting slurry was treated in portions over a five minute period with solid NaBH4 (0.97 g, 25.6 mmole). The resulting foaming slurry was stirred and heated at reflux for 1 hr. The reaction was deemed complete by LC-MS. The reaction mixture was cooled to room temperature and concentrated in vacuo to an oily residue. The residue was dissolved in CH2Cl2 and applied to an 80 g silica gel column. The column was eluted with a gradient of hexane/acetone, 90/10 to 20/80 over 32 minutes. The fractions containing product were pooled and concentrated in vacuo giving the title compound as a white solid, 3.14 g, 67%.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. concentrationconcentrated in vacuo to an oily residue
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washThe column was eluted with a gradient of hexane/acetone, 90/10 to 20/80 over 32 minutes
  6. additionThe fractions containing product
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3a907873eee41348e416c9d4e0f741c
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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