반응 #956967

반응 방정식

Boc-piperazine

triethylamine

Mono methyl fumarate

oxalyl chloride

→

(E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate

수율 21.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   기타(1 h)
2. 2
   기타The resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred at room temperature for 1 h
4. 4
   세척washed with brine
5. 5
   건조The organic layer was dried (Na2SO4)
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by chromatography (CH2Cl2)

실험 절차

Mono methyl fumarate (650 mg, 5.0 mmol) was taken up in 10 mL of CH2Cl2 and oxalyl chloride (420 μL, 5.0 mmol) was added. After a few drops of DMF was added, the reaction mixture was stirred at room temperature until all gas evolution had ceased (1 h). This freshly prepared solution of acid chloride was then added dropwise at 0° C. to a solution containing Boc-piperazine (930 mg) and triethylamine (1.0 mL, 7.5 mmol) in 20 mL of CH2Cl2. The resulting reaction mixture was stirred at room temperature for 1 h and washed with brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded 310 mg of (E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate (21% yield).

출처