Potassium Iodide → 4'-{3-[(3S)-3-hydroxypyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrile

HRID 1057781Notes

Reaction equation

HRID 1057781 reaction equation
N[C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:3]1.N1CC[C@H]([OH:30])C1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[OH:30][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 99231474'-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 99231864'-{3-[(3S)-3-hydroxypyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrileYield 61%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile (180 mg, 0.65 mmol), (3S)-3-pyrrolidinol (57 mg, 0.65 mmol), potassium carbonate (140 mg) and potassium iodide (180 mg) in 20 mL of 2-butanone were heated at 110° C. for 72 hours. The mixture was evaporated under reduced pressure and the residue was purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (61 % yield).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customthe residue was purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)

Sources & evidence

ORD record
ord-e0eb991ba91a438dae2747fcfcd27bc0
Source dataset
uspto-grants-2003_02
Patent number
US06515013B2

Reaction notes

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