Reacción #487547

Ecuación de reacción

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

carbonyl diimidazole

4-bromoisoindole

→

solid

Rendimiento 79.4%

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

Rendimiento 79.4%

Disolventes

N,N-dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling down
2. 2
   Extracciónthe reaction mixture was extracted with 50 mL of EtOAc
3. 3
   Lavadowashed with water, brine
4. 4
   Secadodried over Na2SO4
5. 5
   FiltraciónAfter filtration and concentration
6. 6
   Otrothe residue was purified by flash column chromatography on silica gel

Procedimiento

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).

Fuente