Lithium Carbonate → 2-chloro-4-[(2S,3S)-3-ethyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]benzonitrile

HRID 907003Notes

Reaction equation

[CH2:1]([C@:3]1([OH:11])[CH2:7][CH2:6][NH:5][C@H:4]1[CH:8]([CH3:10])[CH3:9])[CH3:2].[Cl:12][C:13]1[CH:20]=[C:19](F)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].C(=O)([O-])[O-].[Li+].[Li+]>>[Cl:12][C:13]1[CH:20]=[C:19]([N:5]2[CH2:6][CH2:7][C@:3]([CH2:1][CH3:2])([OH:11])[C@@H:4]2[CH:8]([CH3:10])[CH3:9])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

Reactant 3

HCID 11125Lithium Carbonate

HCID 1090002-Chloro-4-fluorobenzonitrile

HCID 59273069(2S,3S)-3-ethyl-2-isopropylpyrrolidin-3-ol

Product 1

HCID 592730052-chloro-4-[(2S,3S)-3-ethyl-3-hydroxy-2-isopropylpyrrolidin-1-yl]benzonitrile

Procedure

By an operation in the same manner as in Example 1 and using (2S,3S)-3-ethyl-2-isopropylpyrrolidin-3-ol 0.5 oxalate (162 mg), 2-chloro-4-fluorobenzonitrile (125 mg) and lithium carbonate (126 mg), the title compound was obtained as pale-brown oil (yield: 151 mg, yield: 65%).

Sources & evidence

ORD record: ord-b78dcf0fbfa44069964c976eab5819b3
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013008B2

Reaction notes

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