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

HRID 421844Notes

Reaction equation

HRID 421844 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([C:19]3[N:23]=[C:22](C(Cl)(Cl)Cl)[O:21][N:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6].[BH4-].[Na+]>CO>[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([C:19]3[N:23]=[CH:22][O:21][N:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 666737671-(4,4-Dimethylpentanoyl)-4-{4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}piperazine

Product 1

HCID 119931891-(4,4-Dimethylpentanoyl)-4-[4-(1,2,4-oxadiazol-3-yl)pyridin-2-yl]piperazineYield 23.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4,4-Dimethylpentanoyl)-4-{4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}piperazine (43 mg) obtained in Example 68-1) was dissolved in methanol (3 mL), and sodium borohydride (46 mg) was added thereto and stirred at room temperature for 1 hour. Then, the solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 7.4 mg of the entitled compound as a colorless oil.

Workup

  1. customThen, the solvent was evaporated away
  2. customthe resulting residue was isolated
  3. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2aedd53531ae478d8bfd3725228d3c2f
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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