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

HRID 906998Notes

Reaction equation

[CH3:1][C@H:2]1[C@@:6]([C:8]([F:11])([F:10])[F:9])([OH:7])[CH2:5][CH2:4][NH:3]1.[Cl:12][C:13]1[CH:20]=[C:19](F)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C(=O)([O-])[O-].[Li+].[Li+]>>[Cl:12][C:13]1[CH:20]=[C:19]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([C:8]([F:9])([F:11])[F:10])[C@@H:2]2[CH3:1])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 1090002-Chloro-4-fluorobenzonitrile

HCID 59273044(2S,3S)-2-methyl-3-(trifluoromethyl)pyrrolidin-3-ol

Product 1

HCID 249866652-chloro-4-[(2S,3S)-3-hydroxy-2-methyl-3-(trifluoromethyl)pyrrolidin-1-yl]benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2-methyl-3-(trifluoromethyl)pyrrolidin-3-ol 0.5 oxalate (200 mg), 2-chloro-4-fluorobenzonitrile (289 mg) and lithium carbonate (138 mg), the title compound was obtained as a colorless solid (yield: 100 mg, yield: 35%).

Sources & evidence

ORD record: ord-e3a5b0b8c784422ebdc5973ada1a0d4c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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