Dichloromethane → HCID 23139059, compound

HRID 1171674Notes

Reaction equation

HRID 1171674 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:13](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:19][C:20]\2=[O:21])=[CH:12][N:11]=[N:10]1)=[O:5])[CH3:2].ClCCl.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[C:13](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:18][CH2:19][CH:20]\2[OH:21])=[CH:12][N:11]=[N:10]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 23138915HCID 23138915, compound

Product 1

HCID 23139059HCID 23139059, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (E)-3-({1-[3-(ethoxycarbonyl)propyl]-1H-1,2,3-triazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (14.48 g) in a mixed solvent of dichloromethane (50 ml) and ethanol (200 ml) was added sodium borohydride (1.13 g) with stirring under ice-cooling. After the resulting mixture was stirred at room temperature for 30 minutes, the reaction was stopped by addition of an aqueous ammonium chloride solution. The product was extracted with ethyl acetate. After the organic layer was washed with a saturated aqueous sodium chloride solution, it was dried over anhydrous magnesium sulfate. Solvents were removed under reduced pressure to afford the title compound (14.63 g, yield: quantitative) as a colourless crystalline solid.

Workup

  1. temperaturecooling
  2. stirringAfter the resulting mixture was stirred at room temperature for 30 minutes
  3. extractionThe product was extracted with ethyl acetate
  4. washAfter the organic layer was washed with a saturated aqueous sodium chloride solution, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-6cbc8c18a29e49adadd555fa3627a2c7
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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