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

HRID 907006Notes

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 775452,4-Difluorobenzonitrile

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

Product 1

HCID 592730814-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]-2-fluorobenzonitrile

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), 2,4-difluorobenzonitrile (139 mg) and lithium carbonate (163 mg), the title compound was obtained as a pale-brown solid (yield: 114 mg, yield: 40%).

Sources & evidence

ORD record: ord-5ae7601e96d845dda0c2ea3d0ea34816
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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