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

HRID 906989Notes

Reaction equation

[CH2:1]([C@:3]1([OH:9])[CH2:7][CH2:6][NH:5][C@H:4]1[CH3:8])[CH3:2].F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[C:19]([F:22])([F:21])[F:20].C(=O)([O-])[O-].[Li+].[Li+]>>[CH2:1]([C@:3]1([OH:9])[CH2:7][CH2:6][N:5]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=2[C:19]([F:20])([F:22])[F:21])[C@H:4]1[CH3:8])[CH3:2]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

HCID 59273028(2S,3S)-3-ethyl-2-methylpyrrolidin-3-ol

Product 1

HCID 592730884-[(2S,3S)-3-ethyl-3-hydroxy-2-methylpyrrolidin-1-yl]-3-(trifluoromethyl)benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-3-ethyl-2-methylpyrrolidin-3-ol 0.5 oxalate (257 mg), 4-fluoro-3-(trifluoromethyl)benzonitrile (419 mg) and lithium carbonate (218 mg), the title compound was obtained as colorless oil (yield: 218 mg, yield: 49%).

Sources & evidence

ORD record: ord-030e99dbec1640f6aac2626eb6d75b95
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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