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

HRID 907007Notes

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 1090002-Chloro-4-fluorobenzonitrile

HCID 59273011(2S,3R)-3-cyclopropyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 592730082-chloro-4-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]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), 2-chloro-4-fluorobenzonitrile (156 mg) and lithium carbonate (163 mg), the title compound was obtained as a pale-brown solid (yield: 130 mg, yield: 43%).

Sources & evidence

ORD record: ord-bf1c5bf37a704cc5bcab1e284afbaf17
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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