تفاعل #167085

معادلة التفاعل

p-TsOH.H2O

water

p-TsOH.H2O

(1-{8-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-1,4-dioxa-7-aza-spiro[4.4]nonane-7-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

→

product

المردود 44.6%

(1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

المردود 44.6%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheating at 60° C.
2. 2
   أخرىall volatiles were removed in vacuo
3. 3
   غسيلwas washed with aqueous sodium bicarbonate solution
4. 4
   تجفيفdried over sodium sulfate
5. 5
   ترشيحFiltration and evaporation of solvents in vacuo
6. 6
   أخرىgives the crude product
7. 7
   أخرىThe crude material was purified via silica gel chromatography (eluent: EtOAc containing 10% MeOH/hexanes)

الإجراء التجريبي

(1-{8-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-1,4-dioxa-7-aza-spiro[4.4]nonane-7-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (230.0 mg, 0.453 mmol) was dissolved in acetone (10 mL) and water (0.2 mL) and p-TsOH.H2O (53 mg, 0.278 mmol) were added. The reaction was heated at 60° C. for 20 hours, after which additional p-TsOH.H2O (53 mg, 0.278 mmol) was added heating at 60° C. was continued. After three days, all volatiles were removed in vacuo. The crude material was taken into EtOAc and was washed with aqueous sodium bicarbonate solution and dried over sodium sulfate. Filtration and evaporation of solvents in vacuo gives the crude product. The crude material was purified via silica gel chromatography (eluent: EtOAc containing 10% MeOH/hexanes) to yield the product (93.9 mg, 0.202 mmol).

المصدر