Synthesis of 4,4-dialkoxy-3-piperidinols. Application to the synthesis of γ-acetate dehydropipecolinonitrile
作者:Meng-Yang Chang、Tein-Wei Lee、Chung-Han Lin
DOI:10.1016/j.tet.2011.04.102
日期:2011.7
N-bromosuccinimide in acetic acid and alkoxide ion-mediated α,α-dialkoxyhydroxylation. Under acidic condition, trimethyl orthoformate-mediated reaction of compound 7a yielded aminodienylester 8 in the presence of Ph3PCHCO2Et. The γ-acetate dehydropipecolinonitrile 4 was also synthesized via boron trifluoride etherate-promoted addition of compound 8 with trimethylsilyl cyanide and N-bromosuccinimide and selective
的4,4-二烷氧基-3- piperidinols合成7是由哌啶-4-酮的α-溴化进行5 与Ñ溴代琥珀酰亚胺在乙酸和醇盐离子介导的α,α-dialkoxyhydroxylation。在酸性条件下, 在Ph 3 P CHCO 2 Et存在下,原甲酸三甲酯介导的化合物7a反应生成氨基二烯基酯8。所述γ-醋酸dehydropipecolinonitrile 4还合成通过三氟化硼醚促进的加成化合物的8与氰化三甲基硅烷和Ñ溴代琥珀酰亚胺和选择性加氢。