Reaktion #59662

Reaktionsgleichung

sodium borohydride

2-thiazolidinone

N-phthalimido-3-bromopropylamine

potassium carbonate

18-crown-6

→

3-(3-Aminopropyl)-2-thiazolidinone

Ausbeute 55.0%

Lösungsmittel

water

isopropanol

acetonitrile

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed about 17 hours
2. 2
   Sonstigesolvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe resulting solid was redissolved in 1 M potassium chloride
4. 4
   SonstigeThe aqueous phase was separated
5. 5
   Extraktionextracted with 2×25 ml dichloromethane
6. 6
   TrocknenThe combined organic fraction was dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigedried in vacuo
9. 9
   SonstigeThe crude product was recrystallized from acetone/methanol
10. 10
    Sonstigeto give 1.54 g (55% yield)
11. 11
    workup.STIRRINGthe solution was stirred at 80° C. for 2 hours
12. 12
    Temperaturthe solution was cooled
13. 13
    Sonstigedried in vacuo
14. 14
    workup.DISSOLUTIONThe product was redissolved in 6 N hydrochloric acid
15. 15
    Waschenwashed with ether (2×30 ml)
16. 16
    Sonstigedried in vacuo
17. 17
    SonstigeThe product was purified via recrystallization from hot water

Vorschrift

To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichloromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered, and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water.

Quelle