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

HRID 37808

反応式

HRID 37808 の反応式
[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]

参加物

3

反応物 2

HCID 8821Ethyl AcrylateHCID 98969Ethyl nipecotate

生成物 1

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

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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.)

出典と根拠

ORDレコード
ord-d33cd4c1758c4021a4d601fa24dcd8c8
出典データセット
uspto-grants-2013_09
特許番号
US08524703B2

関連ノート

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