Reaktion #544234

Reaktionsgleichung

product

1-[3-(7-Carboxy-5,11-dihydro[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]-4-(4-chlorophenyl)piperidin-4-ol

sodium iodide

potassium carbonate

cyclohexyl 1-chloroethyl carbonate

→

titled compound

Ausbeute 116.7%

4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-(1-cyclohexyloxycarbonyloxy)ethyloxycarbonyl[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidin-4-ol dihydrochloride

Ausbeute 116.7%

Lösungsmittel

dimethylformamide

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic layer was separated
2. 2
   Waschenwashed with saturated aqueous sodium chloride
3. 3
   Trocknendried with magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:3)
6. 6
   workup.DISSOLUTIONThe obtained oil was dissolved with ethyl acetate, and 4 N hydrochloric acid ethyl acetate solution (0.8 ml)
7. 7
   workup.ADDITIONwas added
8. 8
   SonstigeThe precipitation
9. 9
   Filtrationwas filtered

Vorschrift

To a solution of product of example 118 (1.1 g) in dimethylformamide (15 ml) were added sodium iodide (0.17 g), potassium carbonate (0.38 g) and cyclohexyl 1-chloroethyl carbonate (J. Antibiotics, 1987, 40, 81.) (0.57 g) at room temperature. The mixture was stirred at 70° C. for 1 hour. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:3). The obtained oil was dissolved with ethyl acetate, and 4 N hydrochloric acid ethyl acetate solution (0.8 ml) was added. The precipitation was filtered to give the titled compound (0.96 g).

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