Reaktion #331545

Reaktionsgleichung

EtOAc

compound 37

2-Chloro-5-nitrobenzene-1-sulfonyl chloride

tert-butyl 1-piperazinecarboxylate

Water

→

compound 38

Ausbeute 83.1%

Tert-butyl 4-(2-chloro-5-nitrophenylsulfonyl)piperazine-1-carboxylate

Ausbeute 83.1%

Lösungsmittel

—

hexanes

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionaqueous layer was extracted twice with DCM
2. 2
   WaschenCombined extracts were sequentially washed with water and brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto afford a yellow solid
7. 7
   SonstigeThe solid was triturated with DCM and hexanes
8. 8
   Filtrationfiltered

Vorschrift

A solution of compound 37 (0.600 g, 2.34 mmol) in DCM (20.00 mL) was added tert-butyl 1-piperazinecarboxylate (0.566 g, 3.04 mmol) and TEA (0.422 mL, 3.04 mmol). The reaction was monitored with TLC (25% EtOAc in hexanes, Rf=0.53). The reaction mixture was complete after stirring at room temperature for 1 hr, as indicated by the absence of the starting material (TLC). Water was added and aqueous layer was extracted twice with DCM. Combined extracts were sequentially washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to afford a yellow solid. The solid was triturated with DCM and hexanes, and then filtered to yield compound 38 as a yellow solid (0.789 g, 100% HPLC purity, 83% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.60 (d, J=3 Hz, 1H), 8.47 (dd, J1=3 Hz, J2=8 Hz, 1H), 8.01 (d, J=8 Hz, 1H), 3.37 (m, 4H), 3.23 (m, 4H), 1.37 (s, 9H).

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