Reaktion #11399

Reaktionsgleichung

1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-t-butoxycarbonylamino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid

K2CO3

1-iodopropane

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titled product

Ausbeute 45.0%

i-Propyl 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-amino-3′,3′-dimethyl-piperidin-1-yl)-4-oxo-quinoline-3-carboxylate

Ausbeute 45.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at the same temperature for 16 hr
2. 2
   EinengenSolvent was concentrated up to dryness and (15 ml) water
3. 3
   workup.ADDITIONwas added to it
4. 4
   Extraktionextracted with chloroform (25 ml×2)
5. 5
   SonstigeOrganic layer was separated
6. 6
   Sonstigedried
7. 7
   Einengenconcentrated
8. 8
   Sonstigepurified on silica column

Vorschrift

In a dry dimethylformaide (15 ml) was taken a mixture of 1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-7-(4′-t-butoxycarbonylamino-3′,3′-dimethylpiperidin-1-yl)-4-oxo-quinoline-3-carboxylic acid (1 g, 1.98 mmole), K2CO3 (0.275 g, 1.98 mmole) was stirred at 70° C. for 7 hr. Added 1-iodopropane (0.5 g, 2.98 mmole) to reaction mixture and stirred at the same temperature for 16 hr. Solvent was concentrated up to dryness and (15 ml) water was added to it and extracted with chloroform (25 ml×2). Organic layer was separated, dried, concentrated, Which was hydrolysied with trifluoroacetic acid in methylene dichloride and purified on silica column to furnish titled product. Yield 45%, m.p 140–42° C., C24H32FN3O4, m/z 446 (M+1).

Quelle