تفاعل #52207

معادلة التفاعل

2,5-dimethoxytetrahydrofuran

sodium hydroxide

Benzylamine hydrochloride

ketomalonic acid

sodium acetate

→

title compound

المردود 46.6%

8-Benzyl-8-azabicyclo[3.2.1]octan-3-one

المردود 46.6%

المذيبات

hydrochloric acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated to 50° C. for further 90 minutes
2. 2
   درجة الحرارةcooled in an ice bath
3. 3
   أخرىThe layers were separated
4. 4
   استخلاصthe aqueous phase extracted with ethyl acetate (3×300 ml)
5. 5
   غسيلThe combined organic extracts were washed with water
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated under reduced pressure
9. 9
   workup.DISTILLATIONThe residual brown oil was distilled under reduced pressure (126°/3 mmHg)

الإجراء التجريبي

A solution of 2,5-dimethoxytetrahydrofuran (50 g, 378 mmol) in hydrochloric acid (0.025 N, 160 ml) was cooled to 0° C. for 16 hours. Benzylamine hydrochloride (65 g, 453 mmol), ketomalonic acid (55 g, 377 mmol) and an aqueous solution of sodium acetate (300 ml, 0.69 M) were added and the reaction stirred at room temperature for one hour. The mixture was heated to 50° C. for further 90 minutes, then cooled in an ice bath and basified to pH12 with 2N sodium hydroxide solution. The layers were separated and the aqueous phase extracted with ethyl acetate (3×300 ml). The combined organic extracts were washed with water, dried (MgSO4), filtered and evaporated under reduced pressure. The residual brown oil was distilled under reduced pressure (126°/3 mmHg) to afford the title compound as an off-white solid (37.81 g).

المصدر