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

HRID 906988Notes

Reaction equation

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

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 27833294-Fluoro-2-methoxybenzonitrile

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

Product 1

HCID 592730754-[(2S,3S)-3-ethyl-3-hydroxy-2-methylpyrrolidin-1-yl]-2-methoxybenzonitrile

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), 4-fluoro-2-methoxybenzonitrile (447 mg) and lithium carbonate (218 mg), the title compound was obtained as colorless oil (yield: 305 mg, yield: 79%).

Sources & evidence

ORD record: ord-c04d94f7245549b4aa9d0e4fc07ee4f2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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