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

HRID 2046683Notes

Reaction equation

[Cl:1][C:2]1[C:9]([Cl:10])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:12][C:13]([C@H:16]1[CH2:20][CH2:19][NH:18][C@H:17]1[CH3:21])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Li+].[Li+]>>[Cl:1][C:2]1[C:9]([Cl:10])=[C:8]([N:18]2[CH2:19][CH2:20][C@H:16]([C:13]([OH:12])([CH3:15])[CH3:14])[C@@H:17]2[CH3:21])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 223785152,3-Dichloro-4-fluorobenzonitrile

HCID 55299039(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine

Product 1

HCID 593705332,3-dichloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]benzonitrile

Procedure

Using 2,3-dichloro-4-fluorobenzonitrile (334 mg), (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (397.3 mg) and lithium carbonate (312 mg), the title compound was obtained as white crystals (yield: 427 mg) by an operation similar to that in Example 3.

Sources & evidence

ORD record: ord-4310e10e0e0c434182ebbd462be7aa85
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592452B2

Reaction notes

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