تفاعل #46453

معادلة التفاعل

H2O

Sec BuLi

3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester

dimethyl sulfide

→

3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm up to room temperature for 30 minutes
2. 2
   أخرىThe organic layer was separated
3. 3
   غسيلwashed with water and brine
4. 4
   تجفيفAfter drying over MgSO4
5. 5
   تركيزthe organic fraction was concentrated in vacuo

الإجراء التجريبي

A solution of 3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester (186 mg, 0.38 mmol) in THF (5 ml) was cooled to −78° C., and Sec-BuLi (1.4 ml, 1.4 M in cyclohexane) was added. After stirring at −78° C. for 20 minutes, 1 ml of dimethyl sulfide was added and the reaction was allowed to warm up to room temperature for 30 minutes. H2O was slowly added, followed by EtOAC. The organic layer was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo to give crude 3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester as an oil (277 mg), which was used without further purification.

المصدر