Lithium Carbonate → 4-[(2S,3S)-3-ethyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 907001Notes

Reaction equation

[CH2:1]([C@:3]1([OH:11])[CH2:7][CH2:6][NH:5][C@H:4]1[CH:8]([CH3:10])[CH3:9])[CH3:2].F[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=1.C(=O)([O-])[O-].[Li+].[Li+]>>[CH2:1]([C@:3]1([OH:11])[CH2:7][CH2:6][N:5]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:22])([F:24])[F:23])[CH:14]=2)[C@H:4]1[CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrile

HCID 59273069(2S,3S)-3-ethyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 592730074-[(2S,3S)-3-ethyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-3-ethyl-2-isopropylpyrrolidin-3-ol 0.5 oxalate (203 mg), 4-fluoro-2-(trifluoromethyl)benzonitrile (189 mg) and lithium carbonate (163 mg), the title compound was obtained as colorless oil (yield: 180 mg, yield: 55%).

Sources & evidence

ORD record: ord-eb76f0e313dc4c61847f96ca4346742d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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