Lithium Carbonate → 2-fluoro-4-[(2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidin-1-yl]benzonitrile

HRID 907013Notes

Reaction equation

[CH3:1][C@H:2]1[C@@:6]([CH:8]=[CH2:9])([OH:7])[CH2:5][CH2:4][NH:3]1.[F:10][C:11]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C(=O)([O-])[O-].[Li+].[Li+]>>[F:10][C:11]1[CH:18]=[C:17]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH:8]=[CH2:9])[C@@H:2]2[CH3:1])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 775452,4-Difluorobenzonitrile

HCID 67389951(2S,3R)-2-methyl-3-vinylpyrrolidin-3-ol

Product 1

HCID 592730802-fluoro-4-[(2S,3R)-3-hydroxy-2-methyl-3-vinylpyrrolidin-1-yl]benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3R)-2-methyl-3-vinylpyrrolidin-3-ol (554 mg), 2,4-difluorobenzonitrile (300 mg) and lithium carbonate (350 mg), the title compound was obtained as a colorless solid (yield: 177 mg, yield: 50%).

Sources & evidence

ORD record: ord-18d6c674523d4875aa61464a1c036ee2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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