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

HRID 1167843Notes

Reaction equation

N[C@@H]1CCN(CCCO[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)C1.[NH:25]1[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C[C:40](=[O:43])[CH2:41][CH3:42]>>[OH:30][C@@H:27]1[CH2:28][CH2:29][N:25]([CH2:42][CH2:41][CH2:40][O:43][C:21]2[CH:22]=[C:17]([C:14]3[CH:13]=[CH:12][CH:11]=[CH:16][CH:15]=3)[CH:18]=[CH:19][C:20]=2[C:23]#[N:24])[CH2:26]1

Participants

Reactant 5

HCID 4875Potassium Iodide

HCID 6569Methyl Ethyl Ketone

HCID 11430Potassium Carbonate

HCID 2759337(R)-3-Pyrrolidinol

HCID 99231474'-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrile

Product 1

HCID 701613863-[(3R)-{3-hydroxypyrrolidinyl]propoxy}[1,1'-biphenyl]-4-carbonitrileYield 69%

Procedure

4′-{3-[(3R)-3-Aminopyrrolidinyl]propoxy}[1,1′-biphenyl]-4-carbonitrile (200 mg, 0.74 mmol), (3R)-3-pyrrolidinol (70 mg, 0.81 mmol), potassium carbonate (152 mg) and potassium iodide (183 mg) in 25 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 (69% yield).

Workup

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

Sources & evidence

ORD record: ord-4466d60a065a43e6ab5e2e4bcb58ec1e
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06620839B2

Reaction notes

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