تفاعل #614883

معادلة التفاعل

cyclohexane ethyl acetate

cyclohexane ethyl acetate

2-methyl-N1-{6-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinyl}alaninamide

Intermediate 129

2-methyl-N1-{6-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinyl}alaninamide

triphosgene

→

title compound

المردود 81.1%

5,5-dimethyl-3-{6[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinyl}-2,4-imidazolidinedione

المردود 81.1%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was then quenched with water
2. 2
   أخرىthe two phases were separated
3. 3
   تجفيفThe organic layer was dried over sodium sulphate
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated
6. 6
   أخرىthe residue was purified by silica gel chromatography (Companion system

الإجراء التجريبي

To a solution of 2-methyl-N1-{6-[(1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-yl)oxy]-3-pyridinyl}alaninamide (Intermediate 129, 100 mg) in dry dichloromethane (10 ml) TEA (0.177 ml, 1.273 mmol) was added and the reaction mixture was cooled to 0° C. At this point a solution of triphosgene (37.8 mg, 0.127 mmol) in dry dichloromethane (2.5 ml) was slowly added (over 30 minutes) and the reaction mixture was stirred for 1 hour at the same temperature. The reaction was then quenched with water and the two phases were separated. The organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by silica gel chromatography (Companion system, with a gradient from cyclohexane/ethyl acetate 8:2 to cyclohexane/ethyl acetate 1:1) to give the title compound as a white solid (40 mg, 0.103 mmol).

المصدر