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

HRID 2046680Notes

Reaction equation

[Cl:1][C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:14][C:15]([C@H:18]1[CH2:22][CH2:21][NH:20][C@H:19]1[CH3:23])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Li+].[Li+]>>[Cl:1][C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([N:20]2[CH2:21][CH2:22][C@H:18]([C:15]([OH:14])([CH3:17])[CH3:16])[C@@H:19]2[CH3:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

Reactant 3

HCID 11125Lithium Carbonate

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

HCID 593705442-Chloro-4-fluoro-3-propylbenzonitrile

Product 1

HCID 593705012-chloro-4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-3-propylbenzonitrile

Procedure

Using 2-chloro-4-fluoro-3-propylbenzonitrile (538 mg), (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (615 mg) and lithium carbonate (259 mg), the title compound was obtained as a yellow solid (yield: 69 mg) by an operation similar to that in Example 3.

Sources & evidence

ORD record: ord-f0b0eb435f394271a3c4c4321e10d368
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592452B2

Reaction notes

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