تفاعل #1253194

معادلة التفاعل

1-t-Butoxycarbonyl-3-oxopiperazine

potassium t-butoxide

1-(4-methylphenylsulfonyloxy)-2-fluoroethane

→

1-t-butoxycarbonyl-4-(2-fluoroethyl)-3-oxopiperazine

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued at the same temperature for 24 hours
3. 3
   أخرىThe solvent is removed
4. 4
   أخرىthe residue partitioned between ethyl acetate and water
5. 5
   غسيلThe organic phase is washed with water
6. 6
   تركيزconcentrated
7. 7
   workup.DISSOLUTIONThe residue is dissolved in isopropanol
8. 8
   workup.ADDITIONdiluted with iso-hexane forming a precipitate which
9. 9
   أخرىis removed by filtration
10. 10
    أخرىThe mixture is chromatographed (silica
11. 11
    غسيلeluting with
12. 12
    درجة الحرارةa gradient increasing in polarity from 0 to 50% isopropanol in iso-hexane)

الإجراء التجريبي

1-t-Butoxycarbonyl-3-oxopiperazine (21.6 g) is dissolved in dry DMF (500 ml) and potassium t-butoxide (24.2 g) is added. The mixture is stirred at 20-25° for 30 minutes, then 1-(4-methylphenylsulfonyloxy)-2-fluoroethane (J. Med. Chem., 23(9), 985-90 (1980), 25.9 g) is added and stirring continued at the same temperature for 24 hours. The solvent is removed and the residue partitioned between ethyl acetate and water. The organic phase is washed with water and concentrated. The residue is dissolved in isopropanol and diluted with iso-hexane forming a precipitate which is removed by filtration. The mixture is chromatographed (silica; eluting with a gradient increasing in polarity from 0 to 50% isopropanol in iso-hexane) to give 1-t-butoxycarbonyl-4-(2-fluoroethyl)-3-oxopiperazine.

المصدر