Reacción #2122492

Ecuación de reacción

3-[1-Methoxy-4-(4-methoxy-benzylsulfanyl)-piperidin-4-yl]-3-oxo-2-(2,4,6-trimethylphenyl)-propionic acid methyl ester

3-[1-methoxy-4-(4-methoxy-benzylsulfanyl)-piperidin-4-yl]-3-oxo-2-(2,4,6-trimethylphenyl)-propionic acid methyl ester

sodium hydroxide

→

4-hydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1-thia-8-aza-spiro[4.5]dec-3-en-2-one

Rendimiento 48.3%

Disolventes

water

trifluoroacetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaon reflux for 18 hours
3. 3
   Extracciónextracted with t-butylmethyl ether
4. 4
   SecadoThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Otrothe solvent evaporated
6. 6
   OtroThe residue was chromatographed on silica gel with ethyl acetate/cyclohexane (1:1

Procedimiento

470 mg 3-[1-Methoxy-4-(4-methoxy-benzylsulfanyl)-piperidin-4-yl]-3-oxo-2-(2,4,6-trimethylphenyl)-propionic acid methyl ester (from Step 6) was dissolved in 15 ml trifluoroacetic acid and heated on reflux for 18 hours. The mixture was cooled to room temperature, diluted with water, the pH adjusted to 4.2 by the addition of aqueous sodium hydroxide, then extracted with t-butylmethyl ether. The organic layer was dried over anhydrous sodium sulfate, and the solvent evaporated. The residue was chromatographed on silica gel with ethyl acetate/cyclohexane (1:1, then 2:1) as a solvent, to yield 156 mg 4-hydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1-thia-8-aza-spiro[4.5]dec-3-en-2-one (compound P2.4) as a solid, mp 67-71° C.

Fuente