Sodium borohydride → 2,2-Dimethylpropyl 4-[4-(1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate

HRID 421826Notes

Reaction equation

HRID 421826 reaction equation
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[CH:9]=2)[N:4]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C>[O:7]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[CH:9]=2)=[N:6]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 119927082,2-Dimethylpropyl 4-{4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

Product 1

HCID 119928022,2-Dimethylpropyl 4-[4-(1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylateYield 52.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropyl 4-[4-(5-trichloromethyl-1,2,4-oxadiazol-3-yl)pyridin-2-yl]-1-piperazinecarboxylate (23.1 mg) obtained in Example 32 was dissolved in methanol (2 mL), and sodium borohydride (10 mg) was added thereto and stirred at room temperature for 10 minutes. Then, the reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=7/3) to obtain 9.1 mg of the entitled compound as a colorless oil.

Workup

  1. customThen, the reaction liquid
  2. washwashed with water and saturated saline water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solvent was evaporated away
  5. customthe resulting residue was isolated
  6. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-ff518cfe6a174c638acca96dbcc5ba34
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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