تفاعل #809356

معادلة التفاعل

potassium tert-butoxide

quinuclidin-3-one

(4-toluenesulfonyl)methyl isocyanide

1,2-dimethoxyethane

→

rac-1-Azabicyclo[2.2.2]octane-3-carbonitrile

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwhile cooling in ice
2. 2
   أخرىdoes not rise above 10° C
3. 3
   أخرىThe solid resulting at RT
4. 4
   ترشيحis filtered off
5. 5
   تركيزThe filtrate is concentrated
6. 6
   أخرىchromatographed on neutral alumina (mobile phase
7. 7
   أخرى22.9 g (103% of theory) of the product are obtained in slightly impure form

الإجراء التجريبي

20.4 g (163 mmol) of quinuclidin-3-one and 41.37 g (211.87 mmol) of (4-toluenesulfonyl)methyl isocyanide are introduced into 435 ml of 1,2-dimethoxyethane and 16 ml of dry ethanol while cooling in ice. 45.72 g (407.45 mmol) of potassium tert-butoxide are slowly added in such a way that the temperature does not rise above 10° C. The mixture is then heated at 40° C. for 2.5 h. The solid resulting at RT is filtered off. The filtrate is concentrated and chromatographed on neutral alumina (mobile phase: initially dichloromethane, then ethyl acetate→ethyl acetate/methanol 50:1). 22.9 g (103% of theory) of the product are obtained in slightly impure form.

المصدر