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

HRID 403690노트

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HRID 403690 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

HCID 3018364Ethyl 3-oxopiperidine-4-carboxylate hydrochloride수율 84%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da92b8fd5ded4564a5da0bad090429ef
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748456B2

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