N-Methylbenzylamine → (2S,4EZ)-N2-benzyl-4-benzylidene-N2-methyl-N1-(3-methylphenyl)-1,2-pyrrolidinedicarboxamide

HRID 1349174Notes

Reaction equation

HRID 1349174 reaction equation
[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15]C(C)(C)C)=O)[C@H:10]([C:20]([OH:22])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1)=C=O.[CH2:33]([NH:40][CH3:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:33]([N:40]([CH3:41])[C:20]([C@@H:10]1[CH2:9][C:8](=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][N:11]1[C:13]([NH:23][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1)=[O:15])=[O:22])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 3

HCID 7669N-MethylbenzylamineHCID 69303m-Tolyl isocyanateHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725527(2S,4EZ)-N2-benzyl-4-benzylidene-N2-methyl-N1-(3-methylphenyl)-1,2-pyrrolidinedicarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 1-isocyanato-3-methylbenzene, and N-benzyl-N-methylamine the title compound was obtained in 68% purity by LC/MS. MS(ESI+): m/z=440.2.

Sources & evidence

ORD record
ord-c4163666e1cd4ff4a3cdba679893988b
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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