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tert-Butyl acetate → Glycine ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | tert-Butyl acetate | HCID 10908 | — |
| 反応物 | 1H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester | HCID 137477 | — |
| 反応物 | Ethyl 2-amino-3-oxobutanoate | HCID 13282896 | — |
| 生成物 | Glycine ethyl ester | HCID 12176 | — |
| 生成物 | 2-Acetylcyclopentanone | HCID 98471 | — |
| 生成物 | ethyl 4-(tert-butyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate | HCID 12039805 | — |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05446157 |
| 出典データセット | uspto-grants-1995_08 |
| ORD ID | ord-fc9ac76aa0df4504b6c3d75b9cf9fc8a |
| 出典メモ | uspto-grants-1995_08 |