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

HRID 906996Notes

Reaction equation

HRID 906996 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[CH:19]=[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[CH:19]=[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

4

Reactant 3

HCID 11125Lithium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 59273025(2S,3S)-2-methyl-3-propylpyrrolidin-3-ol

Product 1

HCID 592730142-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2,3-dimethylpyrrolidin-3-ol 0.5 oxalate (1.50 g), 2-chloro-4-fluorobenzonitrile (3.04 g) and lithium carbonate (1.04 g), the title compound was obtained as a colorless solid (yield: 1.70 g, yield: 72%).

Sources & evidence

ORD record
ord-bd28ed6f0146444dabe6d102bc64f039
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

Loading…