Sodium borohydride → HCID 23447575, compound

HRID 1840554Notes

Reaction equation

HRID 1840554 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[C:29](=O)[C:28]4[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:27]=4[O:26][CH:25]=3)(=[O:23])=[O:22])[CH2:17][C:16]2=[O:36])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([N:4]1[CH2:5][CH2:6][C:7]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH2:25][O:26][C:27]4[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:28]=4[CH:29]=3)(=[O:22])=[O:23])[CH2:17][C:16]2=[O:36])([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23447599HCID 23447599, compound

Product 1

HCID 23447575HCID 23447575, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the obtained 1-(1-acetyl-4-methoxycarbonylpiperidin-4-ylmethyl)-4-(7-chloro-4-oxo-4H-benzopyran-3-sulfonyl)-2-piperazinone (1.10 g) in methanol (20 ml) was added sodium borohydride (116 mg), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated, and to the residue was added citric acid solution. The mixture was extracted with ethyl acetate, washed with brine, dried and concentrated, and the residue was dissolved in dichloromethane (20 ml). To the solution were added triethylamine (1.23 g) and methanesulfonyl chloride (420 mg), and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with dichloromethane, washed with citric acid solution and brine, dried and concentrated, and the residue was purified with silica gel column chromatography (ethyl acetate:methanol=20:1) to give colorless solid of the title compound (790 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionto the residue was added citric acid solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  8. additionTo the solution were added triethylamine (1.23 g) and methanesulfonyl chloride (420 mg)
  9. stirringthe mixture was stirred at room temperature for 1 hour
  10. additionThe reaction solution was diluted with dichloromethane
  11. washwashed with citric acid solution and brine
  12. customdried
  13. concentrationconcentrated
  14. customthe residue was purified with silica gel column chromatography (ethyl acetate:methanol=20:1)

Sources & evidence

ORD record
ord-243eb02fd7324f5dabc0ec10bf48e988
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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