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Synthesis of 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2016-03-29 , DOI: 10.1134/s1070428016010164
A. Yu. Mandzhulo , N. A. Mel’nichuk , V. N. Fetyukhin , M. V. Vovk

N-Boc-protected 8-azaspiro[bicyclo[3.2.1]octane-3,2′-oxirane] reacted with primary aliphatic amines through opening of the epoxide ring with formation of the corresponding amino alcohols which were converted into N-chloroacetyl derivatives. The latter underwent cyclization to N-Boc-protected 4′-alkyl-8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-ones by the action of sodium hydride in DMF, and subsequent treatment with hydrogen chloride in ethyl acetate afforded 8-azaspiro[bicyclo[3.2.1]octane-3,2′-morpholin]-5′-one hydrochlorides.

中文翻译:

4'-烷基-8-氮杂螺[双环[3.2.1]辛烷-3,2'-吗啉] -5'-一的合成

N -Boc保护的8-azaspiro [双环[3.2.1]辛烷-3,2'-环氧乙烷]通过环的开环与脂肪族伯胺反应,形成相应的氨基醇,并将其转化为N-乙酰基衍生物。后者后行环化成Ñ -Boc保护的4'-烷基-8-氮杂螺[二环[3.2.1]辛烷-3,2'-吗啉] -5'-酮由氢化钠在DMF中的动作,以及随后的用乙酸乙酯中的氯化氢处理,得到8-氮杂螺[双环[3.2.1]辛烷-3,2'-吗啉] -5'-一盐酸盐。
更新日期:2016-03-29
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