تفاعل #8858

معادلة التفاعل

tert-butyldimethylsilyl chloride

tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

imidazole

→

title compound

المردود 86.2%

tert-Butyl 1-vinyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

المردود 86.2%

المذيبات

ether

sodium bicarbonate

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted twice with ether
2. 2
   غسيلThe combined ether layers were washed with brine
3. 3
   تجفيفdried over sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by flash chromatography
7. 7
   غسيلeluting with 5% ethyl acetate in hexanes

الإجراء التجريبي

To a solution of tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.462 g, 1.64 mmoL) from Step A in DMF (8 mL) was added imidazole (0.335 mg, 4.92 mmol) and then tert-butyldimethylsilyl chloride (0.370 g, 2.4 mmol). The reaction was stirred at room temperature for 20 h and then diluted with ether and sodium bicarbonate solution. The mixture was extracted twice with ether. The combined ether layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% ethyl acetate in hexanes to afford the title compound (0.56 g) as a mixture of isomers.

المصدر