Lithium Carbonate → 4-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2,6-difluorobenzonitrile

HRID 907009Notes

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[CH:21]=[C:20](F)[CH:19]=[C:18]([F:23])[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:21]=[C:14]([F:13])[C:15]([C:16]#[N:17])=[C:18]([F:23])[CH:19]=3)[C@H:5]2[CH3:9])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 7371772,4,6-Trifluorobenzonitrile

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

Product 1

HCID 592730374-[(2S,3R)-3-cyclopropyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2,6-difluorobenzonitrile

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 (200 mg), 2,4,6-trifluorobenzonitrile (288 mg) and lithium carbonate (180 mg), the title compound was obtained as a colorless solid (yield: 172 mg, yield: 51%).

Sources & evidence

ORD record: ord-e21d46331484419da21f11daae5d02b7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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