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

HRID 906993Notes

Reaction equation

[CH3:1][C@H:2]1[C@@:6]([CH2:8][CH2:9][CH3:10])([OH:7])[CH2:5][CH2:4][NH:3]1.F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][CH3:21])[CH:13]=1.C(=O)([O-])[O-].[Li+].[Li+]>>[OH:7][C@@:6]1([CH2:8][CH2:9][CH3:10])[CH2:5][CH2:4][N:3]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([O:20][CH3:21])[CH:13]=2)[C@H:2]1[CH3:1]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 27833294-Fluoro-2-methoxybenzonitrile

HCID 59273025(2S,3S)-2-methyl-3-propylpyrrolidin-3-ol

Product 1

HCID 592730654-[(2S,3S)-3-hydroxy-2-methyl-3-propylpyrrolidin-1-yl]-2-methoxybenzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-2-methyl-3-propylpyrrolidin-3-ol 0.5 oxalate (250 mg), 4-fluoro-2-methoxybenzonitrile (399 mg) and lithium carbonate (195 mg), the title compound was obtained as colorless oil (yield: 303 mg, yield: 83%).

Sources & evidence

ORD record: ord-cba307f165434169a8884edeb1896816
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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