تفاعل #75600

معادلة التفاعل

ammonium chloride

allylmagnesium bromide

tert-butyl 4-oxo-1-piperidinecarboxylate

→

tert-butyl 4-allyl-4-hydroxy-1-piperidinecarboxylate

المذيبات

—

ice methanol

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىThe diethyl ether layer was recovered
2. 2
   غسيلwashed with brine
3. 3
   تجفيفIt was dried over anhydrous magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىThe filtrate was evaporated
6. 6
   أخرىthe resulting residue was purified by silica gel column chromatography

الإجراء التجريبي

800 ml solution of 25.0 g tert-butyl 4-oxo-1-piperidinecarboxylate in diethyl ether was cooled in ice/methanol, and 138 ml solution of allylmagnesium bromide (1 M in diethyl ether) was added dropwise thereinto. The reaction mixture was stirred for 3 hr and 10 min. The reaction solution was poured into a mixture of saturated aqueous ammonium chloride and ice. The diethyl ether layer was recovered and washed with brine. It was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated, and the resulting residue was purified by silica gel column chromatography to give 15.9 g of tert-butyl 4-allyl-4-hydroxy-1-piperidinecarboxylate.

المصدر