Ethyl Acrylate → 1-Piperidinepropanoic acid, 3-(ethoxycarbonyl)-, ethyl ester

HRID 37808

반응식

HRID 37808 반응식
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>>[CH2:17]([O:16][C:12](=[O:15])[CH2:13][CH2:14][N:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1)[CH3:18]

참가 물질

3

반응물 2

HCID 8821Ethyl AcrylateHCID 98969Ethyl nipecotate

생성물 1

HCID 115651151-Piperidinepropanoic acid, 3-(ethoxycarbonyl)-, ethyl ester

반응 조건

온도
80 °C

실험 절차

A 25 mL round-bottom flask was charged with ethyl nipecotate (8.0 mL, 51.5 mmol, Aldrich) and ethyl acrylate (6.0 mL, 55.4 mmol, Aldrich). The flask was purged with nitrogen and the mixture was heated to 80° C. for 20 hours. The excess ethyl acrylate was removed under reduced pressure. The remaining residue was purified by distillation (0.9 Ton, 122° C.) to provide the title compound: 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.27 (m, 6H), 1.41-1.59 (m, 2H), 1.69-1.74 (m, 1H), 1.90-1.94 (m, 1H), 2.05 (td, J=10.9, 2.9 Hz, 1H), 2.05 (t, J=10.7 Hz, 1H), 2.46-2.56 (m, 3H), 2.69-2.76 (m, 3H), 2.95-2.98 (m, 1H), 4.10-4.16 (m, 4H); 13C NMR (100 MHz, CDCl3) δ ppm 14.14, 14.15, 24.51, 26.78, 32.61, 41.80, 53.37, 53.79, 55.12, 60.28, 60.23, 172.50, 174.03; MS (DCI/NH3) m/z 258 (M+H)+.

후처리

  1. customThe flask was purged with nitrogen
  2. customThe excess ethyl acrylate was removed under reduced pressure
  3. distillationThe remaining residue was purified by distillation (0.9 Ton, 122° C.)

출처 및 근거

ORD 기록
ord-d33cd4c1758c4021a4d601fa24dcd8c8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524703B2

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