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

HRID 906995Notes

Reaction equation

[CH3:1][C@H:2]1[C@@:6]([CH2:8]CC)([OH:7])[CH2:5][CH2:4][NH:3]1.[Cl:11][C:12]1[C:19]([CH3:20])=[C:18](F)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[Li+].[Li+]>>[Cl:11][C:12]1[C:19]([CH3:20])=[C:18]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH3:8])[C@@H:2]2[CH3:1])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 445509712-Chloro-4-fluoro-3-methylbenzonitrile

HCID 59273025(2S,3S)-2-methyl-3-propylpyrrolidin-3-ol

Product 1

HCID 592730182-chloro-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 (260 mg), 2-chloro-4-fluoro-3-methylbenzonitrile (550 mg) and lithium carbonate (240 mg), the title compound was obtained as a colorless solid (yield: 320 mg, yield: 75%).

Sources & evidence

ORD record: ord-825260c3ebbc447c9a7022a05ea741b2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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