反応 #487547

反応方程式

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

carbonyl diimidazole

4-bromoisoindole

→

solid

収率 79.4%

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

収率 79.4%

溶媒

N,N-dimethylacetamide

反応条件

後処理

1. 1
   温度After cooling down
2. 2
   抽出the reaction mixture was extracted with 50 mL of EtOAc
3. 3
   洗浄washed with water, brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過After filtration and concentration
6. 6
   その他the residue was purified by flash column chromatography on silica gel

実験手順

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).

出典