Reaktionsgleichung
[CH:1]([O:4][C:5]([C:7]1[C:12]([CH2:13][O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6])([CH3:3])[CH3:2].[SiH3]O[SiH3]>>[CH:1]([O:4][C:5]([CH:7]1[CH:12]([CH2:13][O:14][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])[CH2:11][CH2:10][CH2:9][NH:8]1)=[O:6])([CH3:3])[CH3:2]Komponenten
Versuchsvorschrift
Hydrogenation of compound 3-(1-ethoxy-ethoxymethyl)-pyridine-2-carboxylic acid isopropyl ester, following the method used for the corresponding silyl ether as in scheme 1, gave the desired product 3-(1-ethoxy-ethoxymethyl)-piperidine-2-carboxylic acid isopropyl ester. The starting pyridine compound (5.1 g, 19.1 mmol) was dissolved in 60 mL of methanol in a pressure hydrogenation vessel to which 2 g of PtO2 was added. The vessel was shaken under 60 psi of hydrogen for 5 days. The suspension was filtered through Celite and the solution was concentrated in vacuo to provide the desired compound, 3-(1-ethoxy-ethoxymethyl)-piperidine-2-carboxylic acid isopropyl ester (5.1 g, ca. 100%). Data: MS 274 (M+1); 1H NMR (300 MHz, CDCl3): δ 5.50 (br. s, 1H, NH), 5.07 (m, 1H, CH of ester), 4.60–4.64 (overlapping q's, J=7.0 Hz, 1 H), 3.41–3.73 (m, 5H), 3.10 (m, 1H), 2.69 (m, 1H), 2.30 (m, 1H), 1.80–1.95 (m, 2H), 1.41–1.63 (m, 3H), 1.19–1.30 (m, 12 H); 13C NMR (CDCl3, 75 MHz): δ 172.4, 172.3, 100.0, 99.9, 68.1, 68.0, 64.4, 63.7, 61.1, 61.0, 60.4, 46.0, 45.9, 36.81, 36.76, 26.3, 26.1, 22.14, 22.07, 22.0, 21.9, 19.92, 19.85, 15.45, 15.39.
Quellen und Nachweise
- ORD-Eintrag
- ord-c5862a52a8664891b478710a61f3baf8
- Quelldatensatz
- uspto-grants-2006_11
- Patentnummer
- US07132551B2
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