Lithium Carbonate → 4-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-2-methoxybenzonitrile

HRID 906984Notes

Reaction equation

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 27833294-Fluoro-2-methoxybenzonitrile

HCID 59556870(2S,3S)-2,3-dimethylpyrrolidin-3-ol

Product 1

HCID 592730864-[(2S,3S)-3-hydroxy-2,3-dimethylpyrrolidin-1-yl]-2-methoxybenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2,3-dimethylpyrrolidin-3-ol 0.5 oxalate (228 mg), 4-fluoro-2-methoxybenzonitrile (317 mg) and lithium carbonate (206 mg), the title compound was obtained as a colorless solid (yield: 170 mg, yield: 49%).

Sources & evidence

ORD record: ord-df6683d38d5c4467afd2ac73ad46b1d0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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