Reaktion #69580

Reaktionsgleichung

1,1-dimethylethyl (2R)-2-methyl-1-piperazinecarboxylate

triethylamine

4-chlorobenzenesulfonyl chloride

→

title compound

Ausbeute 78.7%

(3R)-1-[(4-chlorophenyl)sulfonyl]-3-methylpiperazine

Ausbeute 78.7%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo the reaction was added resin
2. 2
   workup.STIRRINGthe mixture stirred for 4 h
3. 3
   FiltrationThe reaction mixture was filtered
4. 4
   Waschenthe filtrate washed with 0.5 M HCl (aq., 100 mL)
5. 5
   Trocknenwas dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent removed in vacuo
8. 8
   workup.DISSOLUTIONThe crude product was dissolved in DCM (40 mL)
9. 9
   workup.ADDITIONTFA (10 mL) was added
10. 10
    workup.STIRRINGThe solution was stirred for 20 min
11. 11
    SonstigeThe solvent was evaporated
12. 12
    Waschenthe residue tajen up in DCM (40 mL) and washed with 50% aqueous sodium bicarbonate (100 mL)
13. 13
    TrocknenThe organic phase was dried (MgSO4)
14. 14
    Filtrationfiltered
15. 15
    Sonstigethe solvent removed in vacuo

Vorschrift

To a solution of 1,1-dimethylethyl (2R)-2-methyl-1-piperazinecarboxylate (1.5 g, 07.5 mmol) in dry DCM (40 mL) was added triethylamine (2.59 mL, 18.8 mmol) and 4-chlorobenzenesulfonyl chloride (3.15 g, 10.5 mmol) and the reaction stirred at room temperature for 48 h. To the reaction was added resin supported-triamine (5 g) and the mixture stirred for 4 h. The reaction mixture was filtered and the filtrate washed with 0.5 M HCl (aq., 100 mL) followed by water (100 mL) before it was dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was dissolved in DCM (40 mL) and TFA (10 mL) was added. The solution was stirred for 20 min. The solvent was evaporated and the residue tajen up in DCM (40 mL) and washed with 50% aqueous sodium bicarbonate (100 mL) followed by water (100 mL). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound (1.62 g).

Quelle