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

HRID 1813927

Reaktionsgleichung

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

Komponenten

Edukt 2

HCID 8821Ethyl Acrylate

HCID 98969Ethyl nipecotate

Produkt 1

HCID 115651151-Piperidinepropanoic acid, 3-(ethoxycarbonyl)-, ethyl esterAusbeute 90,2 %

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Ethyl 3-piperidinecarboxylate (3.14 g, 20 mmol) was dissolved in ethyl acrylate (2.50 g, 25 mmol) and stirred at 80° C. (12 h), and then the reaction was concentrated in vacuo, and purified by PTLC (EtOAc/hexanes=3/1) to give 15a (4.64 g, 90%) as a pale yellow oil: Rf 0.51 (EtOAc/hexanes=3/1); IR (neat) 2944, 2806, 1735, 1455, 1376, 1309 cm−1; 1H NMR (CDCl3) δ 1.17-1.22 (m, 6H), 1.35-1.51 (m, 2H), 1.62-1.68 (m, 1H), 1.83-1.89 (m, 1H), 1.95-2.02 (m, 1H), 2.11-2.18 (m, 1H), 2.40-2.50 (m, 3H), 2.62-2.70 (m, 3H), 2.91 (dd, J=1.8, 8.1 Hz, 1H), 4.03-4.12 (m, 4H); 13C NMR (CDCl3) 14.3 (2C), 24.7, 26.9, 32.5, 41.9, 53.5, 53.9, 55.3, 60.3, 60.4, 172.6, 174.1 ppm; MS (+CI) 258 [M+1]+; Mr (+CI) 258.170 30 [M+1]+ (calcd for C13H24NO4 258.170 53).

Aufarbeitung

concentrationthe reaction was concentrated in vacuo
custompurified by PTLC (EtOAc/hexanes=3/1)

Quellen und Nachweise

ORD-Eintrag: ord-18cddc498946409e991d0c50143a87a0
Quelldatensatz: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06875774B2

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