반응 #487547

반응 방정식

(2S,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

carbonyl diimidazole

4-bromoisoindole

→

solid

수율 79.4%

(2S,4R)-1-tert-butyl 2-methyl 4-(4-bromoisoindoline-2-carbonyloxy)pyrrolidine-1,2-dicarboxylate

수율 79.4%

용매

N,N-dimethylacetamide

반응 조건

후처리

1. 1
   온도After cooling down
2. 2
   추출the reaction mixture was extracted with 50 mL of EtOAc
3. 3
   세척washed with water, brine
4. 4
   건조dried over Na2SO4
5. 5
   여과After filtration and concentration
6. 6
   기타the residue was purified by flash column chromatography on silica gel

실험 절차

To a solution containing 0.5 g of (2S,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (2 mmol) in 5 mL of N,N-dimethylacetamide, was added 370 mg of carbonyl diimidazole (1.1 equiv.). The reaction was heated at 60° C. for 1 hr, then 400 mg of 4-bromoisoindole (2 mmol) was added. The reaction was continued at 60° C. overnight. After cooling down, the reaction mixture was extracted with 50 mL of EtOAc, and washed with water, brine, and dried over Na2SO4. After filtration and concentration, the residue was purified by flash column chromatography on silica gel using heptanes/EtOAc (v/v 5/2), giving white solid 745 mg (79%). LC-MS: m/z=369.2 (ES+, M+1-Boc).

출처