1-(2-Chloro-4-pyrimidinyl)-3-ethyl-2-oxo-3-pyrrolidinecarbonitrile → (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile

HRID 714791Notes

Reaction equation

HRID 714791 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1>CCCCCC.CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@:10]([CH2:15][CH3:16])([C:13]#[N:14])[C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 1178407381-(2-Chloro-4-pyrimidinyl)-3-ethyl-2-oxo-3-pyrrolidinecarbonitrile

Product 1

HCID 117840665(3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrileYield 44.9%

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

1-(2-Chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (7.8 g) obtained in Step A of Example 2 was resolved by HPLC (column: CHIRALPAK IC, 50 mmID×500 mmL, manufactured by Daicel Chemical Industries, mobile phase: hexane/2-propanol=200/800) to give the title compound (3.5 g) having a shorter retention time.

Sources & evidence

ORD record
ord-72ccd12b064f4b13a3935b20b9e2415b
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…