N-Methylmaleimide → 4-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-2-methyl-3a,4,6,9,9a,9b-hexahydro-pyrrolo[3,4-a]indolizine-1,3-dione

HRID 540646Notes

Reaction equation

HRID 540646 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]=O)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:18][N:19]1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1=[O:25].Cl.[NH:27]1[CH2:32][CH:31]=[CH:30][CH2:29][CH:28]1C(O)=O>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[CH:16]3[N:27]4[CH:32]([CH2:31][CH:30]=[CH:29][CH2:28]4)[CH:21]4[C:20](=[O:25])[N:19]([CH3:18])[C:23](=[O:24])[CH:22]34)=[N:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 70261N-MethylmaleimideHCID 677837002-Pyridinecarboxylic acid, 1,2,3,6-tetrahydro-, hydrochloride (1:1)HCID 86676729(E)-3-[5-(3-Fluorophenyl)pyridin-2-yl]propenal

Product 1

HCID 534925684-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-2-methyl-3a,4,6,9,9a,9b-hexahydro-pyrrolo[3,4-a]indolizine-1,3-dione

Procedure

The title compound is prepared analogously from 100 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 49 mg of N-methylmaleimide and 58 mg of 1,2,3,6-tetrahydropyridine-2-carboxylic acid hydrochloride. The crude product is purified by column chromatography (silica gel, MeOH:DCM=2:98). In this manner, 3 pure fractions are isolated as racemic mixtures.

Workup

  1. customThe crude product is purified by column chromatography (silica gel, MeOH:DCM=2:98)
  2. customIn this manner, 3 pure fractions are isolated as racemic mixtures

Sources & evidence

ORD record
ord-833ccda15afd4036a5e11f5614a86241
Source dataset
uspto-grants-2014_10
Patent number
US08871798B2

Reaction notes

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