Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → Ethyl 3-oxopiperidine-4-carboxylate hydrochloride

HRID 403690ノート

反応式

HRID 403690 の反応式
[ClH:1].C([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:11](=[O:20])[CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[ClH:1].[O:20]=[C:11]1[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14][NH:9][CH2:10]1

参加物

4

反応物 1

HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride

生成物 1

HCID 3018364Ethyl 3-oxopiperidine-4-carboxylate hydrochloride収率 84%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
50 °C

実験手順

To a suspension of 1.0 g of Pd—C (10 wt. %) was added ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride (10.0 g, 33.58 mmol) (Sigma-Aldrich) dissolved in Ethanol (120 mL). The reaction mixture was then heated at 50° C. under a hydrogen atmosphere (balloon) at atmospheric pressure and followed by HPLC and UPLC-MS. After 4 h at 50° C., the analyses revealed full conversion of the reaction. After cooling to room temperature, the crude mixture was filtered through celite. The celite was washed with EtOH and the filtrate was concentrated in vacuo to give the desired ethyl 3-oxopiperidine-4-carboxylate hydrochloride as an off-white solid (5.84 g, 28.12 mmol, 84% yield). 1HNMR (500 MHz, DMSO-d6): 1.25 (t, J 7.3 Hz, 3H); 2.58 (t, J 6.3 Hz, 2H); 3.26 (t, J 6.3 Hz, 2H); 3.67 (s, 2H), 7.22 (q, J 7.3 Hz, 2H); 9.50 (s, br, 1H); 11.90 (s, br, 1H).

後処理

  1. customconversion of the reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationthe crude mixture was filtered through celite
  4. washThe celite was washed with EtOH
  5. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-da92b8fd5ded4564a5da0bad090429ef
出典データセット
uspto-grants-2014_06
特許番号
US08748456B2

反応ノート

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