Réaction #487547

Équation de réaction

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

carbonyl diimidazole

4-bromoisoindole

→

solid

Rendement 79.4%

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

Rendement 79.4%

Solvants

N,N-dimethylacetamide

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling down
2. 2
   Extractionthe reaction mixture was extracted with 50 mL of EtOAc
3. 3
   Lavagewashed with water, brine
4. 4
   Séchagedried over Na2SO4
5. 5
   FiltrationAfter filtration and concentration
6. 6
   Autrethe residue was purified by flash column chromatography on silica gel

Mode opératoire

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).

Source