Lithium Carbonate → 4-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-5-methyl-2-(trifluoromethyl)benzonitrile

HRID 2046684Notes

Reaction equation

F[C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[OH:15][C:16]([C@H:19]1[CH2:23][CH2:22][NH:21][C@H:20]1[CH3:24])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Li+].[Li+]>>[OH:15][C:16]([C@H:19]1[CH2:23][CH2:22][N:21]([C:2]2[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=2)[C@H:20]1[CH3:24])([CH3:18])[CH3:17]

Participants

Reactant 3

HCID 11125Lithium Carbonate

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

HCID 59370511HCID 59370511, compound

Product 1

HCID 593704984-[(2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidin-1-yl]-5-methyl-2-(trifluoromethyl)benzonitrile

Procedure

Using 4-fluoro-5-methyl-2-(trifluoromethyl)benzonitrile (89 mg), (2S,3S)-3-(1-hydroxy-1-methylethyl)-2-methylpyrrolidine 1/2 oxalate (100 mg) and lithium carbonate (78 mg), the title compound was obtained as a colorless solid (yield: 17 mg) by an operation similar to that in Example 3.

Sources & evidence

ORD record: ord-dfc0a7a713d440c7b026f541f15bad37
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592452B2

Reaction notes

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