Lithium Carbonate → 4-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 907005Notes

Reaction equation

HRID 907005 reaction equation
[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9]([CH3:11])[CH3:10])[CH2:3][CH2:2]1.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1.C(=O)([O-])[O-].[Li+].[Li+]>>[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][N:6]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:23])([F:25])[F:24])[CH:15]=3)[C@H:5]2[CH:9]([CH3:10])[CH3:11])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 11125Lithium CarbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 59273011(2S,3R)-3-cyclopropyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 592730514-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3R)-3-cyclopropyl-2-isopropylpyrrolidin-3-ol 0.5 oxalate (215 mg), 4-fluoro-2-(trifluoromethyl)benzonitrile (189 mg) and lithium carbonate (163 mg), the title compound was obtained as a pale-brown solid (yield: 227 mg, yield: 67%).

Sources & evidence

ORD record
ord-ce6a09c3f9514572bcd697b98f5a5422
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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