2-Methylpyridin-3-ol → 2-methyl-3-(N-t-butoxycarbonyl-2-(R)-azetidinylmethoxy)pyridine

HRID 1416608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1416608
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[C:20](O)=[CH:19][CH:18]=[CH:17][N:16]=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:14][C:15]1[C:20]([O:13][CH2:12][C@H:9]2[CH2:10][CH2:11][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:19][CH:18]=[CH:17][N:16]=1

Komponenten

4

Edukt 3

HCID 707192-Methylpyridin-3-olHCID 5462977Diethyl azodicarboxylateHCID 11074142(R)-1-Boc-2-azetidinemethanol

Produkt 1

HCID 213096592-methyl-3-(N-t-butoxycarbonyl-2-(R)-azetidinylmethoxy)pyridineAusbeute 55,4 %

Versuchsvorschrift

An ice cooled solution of the compound from step 41a (0.151 g,0.81 mmol) was allowed to react with 2-methyl-3-hydroxypyridine (0.092 g, 0.85 mmol) under the conditions of Example 2a, except that DEAD was replaced by di-t-butyl azodicarbonate, to yield the title compound (0.125 g, 55%). MS (DCI/NH3) m/e: 279 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.11 (dd, J=4.6, 1.3 Hz, 1H), 7.20-7.10 (m, 2H), 4.54-4.53 (m, 1H), 4.36-435 (m, 1H), 4.09 (dd, J=10.0, 2.6 Hz, 1H), 3.95-3.88 (m, 2H), 2.55 (s, 3H), 2.42-2.30 (m, 2H), 1.40 (s, 9H).

Quellen und Nachweise

ORD-Eintrag
ord-3c2468721e0a480fa6dbeb8db1367c2f
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05914328

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