Реакция #487547

Уравнение реакции

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

carbonyl diimidazole

4-bromoisoindole

→

solid

Выход 79.4%

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

Выход 79.4%

Растворители

N,N-dimethylacetamide

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling down
2. 2
   Экстракцияthe reaction mixture was extracted with 50 mL of EtOAc
3. 3
   Промывкаwashed with water, brine
4. 4
   Сушкаdried over Na2SO4
5. 5
   ФильтрацияAfter filtration and concentration
6. 6
   Другоеthe residue was purified by flash column chromatography on silica gel

Методика

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).

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