(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile → (S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propanenitrile

HRID 874070Notes

Reaction equation

HRID 874070 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]#[N:16])[CH:10]=[N:11][CH:12]=1>CO.[Pd]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][C:15]#[N:16])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 86659932(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile

Product 1

HCID 86659933(S)-3-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yl)propanenitrileYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-3-(5-(1-Methylpyrrolidin-2-yl)pyridin-3-yl)acrylonitrile (preparation 2) (185 mg, 0.87 mmol) and 5% Pd/C (50 mg) in MeOH (5 mL) were stirred under an atmosphere of hydrogen for 72 hours. The reaction mixture was filtered through Celite then the solvent evaporated. The crude product was purified by flash chromatography (5% [20% ammonia in MeOH] in DCM) to give the title compound as a pale yellow oil (141 mg, 75%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent evaporated
  3. customThe crude product was purified by flash chromatography (5% [20% ammonia in MeOH] in DCM)

Sources & evidence

ORD record
ord-1eb61d0a62c54ee99e5831e557af821f
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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