Lithium Carbonate → 4-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile

HRID 907011Notes

Reaction equation

[CH:1]1([C@:4]2([OH:12])[CH2:8][CH2:7][NH:6][C@H:5]2[CH:9](C)C)[CH2:3][CH2:2]1.[F:13][C:14]1[C:21]([CH3:22])=[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])[C:21]=3[CH3:22])[C@H:5]2[CH3:9])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 113441192,4-Difluoro-3-methylbenzonitrile

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

Product 1

HCID 592730774-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3R)-3-cyclopropyl-2-methylpyrrolidin-3-ol 0.5 oxalate (260 mg), 2,4-difluoro-3-methylbenzonitrile (364 mg) and lithium carbonate (234 mg), the title compound was obtained as a colorless solid (yield: 106 mg, yield: 24%).

Sources & evidence

ORD record: ord-4ea5448d353f47dcb66cbe757a047494
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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