Lithium Carbonate → 4-[(2S,3S)-3-ethyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-fluorobenzonitrile

HRID 906986Notes

Reaction equation

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 775452,4-Difluorobenzonitrile

HCID 59273028(2S,3S)-3-ethyl-2-methylpyrrolidin-3-ol

Product 1

HCID 592730784-[(2S,3S)-3-ethyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-fluorobenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-3-ethyl-2-methylpyrrolidin-3-ol 0.5 oxalate (257 mg), 2,4-difluorobenzonitrile (411 mg) and lithium carbonate (218 mg), the title compound was obtained as a colorless solid (yield: 250 mg, yield: 68%).

Sources & evidence

ORD record: ord-a05fd951e8144702a5c492e38efa3db0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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