反应详情

温度

80 °C

A mixture of 569 mg of crude tert-butyl (3RS,4RS)-4-[4-(2-methylsulphonyloxy-ethoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate and 650 mg of sodium azide in 20 ml of dimethyl sulphoxide was stirred at 80° C. for 3.5 hours. Subsequently, this reaction solution was poured into 50 ml of an ice/water mixture and extracted three times with ethyl acetate. The organic phases were washed with water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The yellow oil (670 mg) was separated on silica gel using a 9:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 271 mg (54% of theory over both steps) of tert-butyl (3RS,4RS)-4-[4-(2-azido-ethoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 503 (M+H)+.

1. extractionextracted three times with ethyl acetate
2. washThe organic phases were washed with water
3. dry with materialdried over magnesium sulphate
4. customevaporated under reduced pressure
5. customdried in a high vacuum
6. customThe yellow oil (670 mg) was separated on silica gel using
7. additiona 9:1 mixture of hexane and ethyl acetate as the eluent