تفاعل #487547

معادلة التفاعل

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

carbonyl diimidazole

4-bromoisoindole

→

solid

المردود 79.4%

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

المردود 79.4%

المذيبات

N,N-dimethylacetamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling down
2. 2
   استخلاصthe reaction mixture was extracted with 50 mL of EtOAc
3. 3
   غسيلwashed with water, brine
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحAfter filtration and concentration
6. 6
   أخرىthe residue was purified by flash column chromatography on silica gel

الإجراء التجريبي

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).

المصدر