Benzyl chloroformate → 1-Benzyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate

HRID 432796ノート

反応式

HRID 432796 の反応式
C(N1CCCC(C(OCC)=O)C1)(=O)C1C=CC=CC=1.[CH3:20][CH2:21][O:22][C:23]([CH:25]1[C:30](=[O:31])[CH2:29][CH2:28][NH:27][CH2:26]1)=[O:24].Cl.C(N(C(C)C)CC)(C)C.Cl[C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44]>>[CH2:46]([O:45][C:43]([N:27]1[CH2:28][CH2:29][C:30](=[O:31])[CH:25]([C:23]([O:22][CH2:21][CH3:20])=[O:24])[CH2:26]1)=[O:44])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

参加物

5

反応物 4

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 1073153-Piperidinecarboxylic acid, 4-oxo-, ethyl ester, hydrochloride (1:1)HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

生成物 1

HCID 446077631-Benzyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate収率 62%

実験手順

The reaction was run in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with commercially available ethyl 4-piperidone-3-carboxylate hydrochloride (203.2 mg; 0.98 mmol), diisopropylethylamine (360 μl; 2.08 mmol), and benzyl chloroformate (141 μl; 0.99 mmol). The crude product was purified by chromatography on silica eluting with 15% ethyl acetate in hexane, giving ethyl 1-benzyloxycarbonyl-4-oxo-3-piperidinecarboxylate (185.5 mg) as a colorless oil. MS m/z (positive ion) 323 (M+NH4+; 75), 306 (MH+; 100), 262 (50).

後処理

  1. customThe crude product was purified by chromatography on silica eluting with 15% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d3c5f8ef66c34329a022e0ed258d0d37
出典データセット
uspto-grants-2003_12
特許番号
US06664271B1

反応ノート

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