tert-Butyl acetate → Glycine ethyl ester

HRID 1757585

Reaktionsgleichung

Reaktionsgleichung von HRID 1757585
[NH2:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:11][C:12]1[CH:16]=[C:15]([CH3:17])[NH:14][C:13]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(O[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C>>[CH3:11][C:12]1[C:16]([C:27]([CH3:30])([CH3:29])[CH3:28])=[C:15]([CH3:17])[NH:14][C:13]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH2:6]([O:5][C:3](=[O:4])[CH2:2][NH2:1])[CH3:7].[CH3:10][C:8]([CH:2]1[C:3](=[O:5])[CH2:13][CH2:12][CH2:11]1)=[O:9]

Komponenten

6

Edukt 3

HCID 10908tert-Butyl acetateHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl esterHCID 13282896Ethyl 2-amino-3-oxobutanoate

Produkt 3

HCID 12176Glycine ethyl esterHCID 984712-AcetylcyclopentanoneHCID 12039805ethyl 4-(tert-butyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate

Versuchsvorschrift

A Knorr cyclization between ethyl a--aminoacetoacetate (prepared in situ) and a 3-alkyl-2,4-pentandione was selected for the preparation of ethyl alkylpyrrole-2 carboxylate derivatives 4b-f, i. Ethyl 3,5-dimethyl-4-tertbutylpyrrole-2-carboxylate 4g was prepared from ethyl 3,5-dimethylpyrrole-2-carboxylate 4a in an alkylation with tert-butyl acetate. In a modification of a Knoevenagel condensation of ethyl N-(3-oxo-1-alkenyl)aminoacetates to ethylpyrrole-2-carboxylates ethyl 3-methyl-2,4,-5,6-tetrahydrocyclopenta[c]pyrrolecarboxylate 4j was obtained by a base catalyzed cyclization of an unisolated enamine 13 (Table IV), in turn obtained from a condensation between glycine ethyl ester and α-acetylcyclopentanone.

Aufarbeitung

  1. customwas obtained by a base

Quellen und Nachweise

ORD-Eintrag
ord-fc9ac76aa0df4504b6c3d75b9cf9fc8a
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05446157

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