Réaction #11399

Équation de réaction

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

Rendement 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

Rendement 45.0%

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred at the same temperature for 16 hr
2. 2
   ConcentrationSolvent was concentrated up to dryness and (15 ml) water
3. 3
   workup.ADDITIONwas added to it
4. 4
   Extractionextracted with chloroform (25 ml×2)
5. 5
   AutreOrganic layer was separated
6. 6
   Autredried
7. 7
   Concentrationconcentrated
8. 8
   Autrepurified on silica column

Mode opératoire

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).

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