Reaktion #60485

Reaktionsgleichung

4-[5-(nonafluorobutane-1-sulfonyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

tributyl(1-ethoxyvinyl)tin

lithium chloride

sodium hydrogencarbonate

→

title compound

Ausbeute 96.4%

4-[5-Acetyl-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester

Ausbeute 96.4%

Lösungsmittel

dimethylformamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through Celite
2. 2
   Einengenthe resultant filtrate was concentrated under reduced pressure
3. 3
   SonstigeThe residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Vorschrift

A mixture of 4-[5-(nonafluorobutane-1-sulfonyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine-1-carboxylic acid t-butyl ester (267 mg, 0.382 mmol) produced in Example (81c), tributyl(1-ethoxyvinyl)tin (0.16 mL, 0.458 mmol), dichlorobis(triphenylphosphine)palladium(II) (41 mg, 0.0573 mmol), lithium chloride (48.6 mg, 1.15 mmol) and dimethylformamide (3 mL) was stirred for 6 hours and 10 minutes at an external temperature of 90° C. under a nitrogen atmosphere. Saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were then added to the reaction mixture. The mixture was filtered through Celite, and the resultant filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 163 mg of the title compound as a colorless oil.

Quelle