Ammonium Chloride → HCID 23138721, compound

HRID 1171665Notes

Reaction equation

HRID 1171665 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[CH:11]=[CH:10][C:9](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:17][C:18]\2=[O:19])=[CH:8]1)=[O:5])C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH3:1][O:3][C:4]([CH2:6][N:7]1[CH:11]=[CH:10][C:9](/[CH:12]=[C:13]2\[CH2:14][N:15]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:16][CH2:17][CH:18]\2[OH:19])=[CH:8]1)=[O:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23138566HCID 23138566, compound

Product 1

HCID 23138721HCID 23138721, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-3-{[1-(ethoxycarbonylmethyl)pyrrol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (19.4 g) in ethanol (100 ml) was added sodium borohydride (3.0 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added aqueous ammonium chloride solution, the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo. To a solution of the residue in methanol (100 ml) was added potassium carbonate (10.6 g), and the resulting mixture was stirred at room temperature for 15 minutes. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo to afford the title compound (12.1 g, yield: 64%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed in vacuo
  6. additionTo a solution of the residue in methanol (100 ml) was added potassium carbonate (10.6 g)
  7. stirringthe resulting mixture was stirred at room temperature for 15 minutes
  8. additionTo the reaction mixture was added water
  9. extractionthe resulting mixture was extracted with ethyl acetate
  10. washThe extract was washed with saturated aqueous sodium chloride solution
  11. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  12. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a2f0a36f3e3c4a92b67eeb95b7c619d1
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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