Water → 3-[4-[1-Hydroxy-2-(2-fluorophenyl)ethyl]piperidino]methyl-1H-pyrazin-2-one

HRID 890096Notes

Reaction equation

HRID 890096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[C:19](=[O:24])[NH:20][CH:21]=[CH:22][N:23]=2)[CH2:13][CH2:12]1)=[O:10].[BH4-].[Na+].O.ClCCl>CO>[OH:10][CH:9]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][C:18]2[C:19](=[O:24])[NH:20][CH:21]=[CH:22][N:23]=2)[CH2:15][CH2:16]1)[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 101933903-[4-[2-(2-Fluorophenyl)acetyl]piperidino]methyl-1H-pyrazin-2-one

Product 1

HCID 222484303-[4-[1-Hydroxy-2-(2-fluorophenyl)ethyl]piperidino]methyl-1H-pyrazin-2-oneYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After suspending 200 mg of 3-[4-[2-(2-fluorophenyl)acetyl]piperidino]methyl-1H-pyrazin-2-one in 6 ml of methanol, an excess of sodium borohydride was added while stirring at room temperature until completion of the reaction. Water was added to the reaction solution and extraction was performed with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. Diethyl ether was added and the insoluble portion was filtered out to obtain the title compound (112 mg, 56% yield).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionDiethyl ether was added
  5. filtrationthe insoluble portion was filtered out

Sources & evidence

ORD record
ord-18312a6b93d944ec985c18ea930e967b
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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