N-Methylmaleimide → 7-Hydroxy-2-methyl-4-[(E)-2-(6-methylpyridin-2-yl)vinyl]hexahydropyrrolo[3,4-a]pyrrolizine-1,3-dione

HRID 540640Notes

Reaction equation

HRID 540640 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](/[CH:8]=[CH:9]/[CH:10]=O)[CH:5]=[CH:4][CH:3]=1.[CH3:12][N:13]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]1=[O:19].[OH:20][C@@H:21]1[CH2:25][NH:24][C@H:23](C(O)=O)[CH2:22]1>>[OH:20][CH:21]1[CH2:22][CH:23]2[N:24]([CH:10](/[CH:9]=[CH:8]/[C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH:16]3[C:17](=[O:18])[N:13]([CH3:12])[C:14](=[O:19])[CH:15]32)[CH2:25]1

Participants

4

Reactant 3

HCID 70261N-MethylmaleimideHCID 440015Cis-4-Hydroxy-L-ProlineHCID 450796953-(6-Methylpyridin-2-yl)prop-2-enal

Product 1

HCID 534924347-Hydroxy-2-methyl-4-[(E)-2-(6-methylpyridin-2-yl)vinyl]hexahydropyrrolo[3,4-a]pyrrolizine-1,3-dione

Procedure

The title compound is prepared analogously from 100 mg of (E)-3-(6-methylpyridin-2-yl)propenal, 75 mg of N-methylmaleimide and 100 mg of cis-4-hydroxy-L-proline.

Sources & evidence

ORD record
ord-159b65e2ded74b23a15e8ebf36d838b2
Source dataset
uspto-grants-2014_10
Patent number
US08871798B2

Reaction notes

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