Lithium Carbonate → 2-fluoro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-3-methylbenzonitrile

HRID 906982Notes

Reaction equation

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 113441192,4-Difluoro-3-methylbenzonitrile

HCID 59556870(2S,3S)-2,3-dimethylpyrrolidin-3-ol

Product 1

HCID 249866642-fluoro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-3-methylbenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2,3-dimethylpyrrolidin-3-ol 0.5 oxalate (228 mg), 2,4-difluoro-3-methylbenzonitrile (321 mg) and lithium carbonate (206 mg), the title compound was obtained as a colorless solid (yield: 194 mg, yield: 56%).

Sources & evidence

ORD record: ord-ebd89c05ba094d24870efc9d72a8b3b9
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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