Lithium Carbonate → 2,6-difluoro-4-[(2S,3S)-3-hydroxy-2-methyl-3-propylpyrrolidin-1-yl]benzonitrile

HRID 906994Notes

Reaction equation

[CH3:1][C@H:2]1[C@@:6]([CH2:8][CH2:9][CH3:10])([OH:7])[CH2:5][CH2:4][NH:3]1.[F:11][C:12]1[CH:19]=[C:18](F)[CH:17]=[C:16]([F:21])[C:13]=1[C:14]#[N:15].C(=O)([O-])[O-].[Li+].[Li+]>>[F:11][C:12]1[CH:19]=[C:18]([N:3]2[CH2:4][CH2:5][C@@:6]([OH:7])([CH2:8][CH2:9][CH3:10])[C@@H:2]2[CH3:1])[CH:17]=[C:16]([F:21])[C:13]=1[C:14]#[N:15]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 7371772,4,6-Trifluorobenzonitrile

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

Product 1

HCID 592730092,6-difluoro-4-[(2S,3S)-3-hydroxy-2-methyl-3-propylpyrrolidin-1-yl]benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2-methyl-3-propylpyrrolidin-3-ol 0.5 oxalate (250 mg), 2,4,6-trifluorobenzonitrile (414 mg) and lithium carbonate (195 mg), the title compound was obtained as colorless oil (yield: 233 mg, yield: 63%).

Sources & evidence

ORD record: ord-50136fd17db64c59b6399432c6387acc
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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