ethyl 2-(1-azabicyclo[2.2.1]hept-3-ylidene)acetate -Drug Synthesis Database

【结构式】

【分子编号】20475

【品名】ethyl 2-(1-azabicyclo[2.2.1]hept-3-ylidene)acetate

【CA登记号】

【分子式】C₁₀H₁₅NO₂

【分子量】181.23464

【元素组成】C 66.27% H 8.34% N 7.73% O 17.66%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The Horner-Emmons reaction of 1-azabicyclo[2.2.1]heptan-3-one (I) with triethyl phosphonoacetate (II) gave conjugated ester (III). Subsequent Michael addition of the oxyanion of ethyl (S)-lactate (IV), generated in the presence of NaH in DMF, with concomitant Dieckmann cyclization, produced ketoester (V). Then, hydrolysis and decarboxylation in boiling 1 N HCl, followed by separation of the syn and anti isomers, yielded the title compound.

参考文献中间体

合成目标

【1】 Wu, E.S.C.; Kover, A.; Semus, S.F.; Synthesis and modeling studies of a potent conformationally rigid muscarinic agonist: 1-Azabicyclo[2.2.1]heptanespirofuranone. J Med Chem 1998, 41, 22, 4181.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	20473	1-azabicyclo[2.2.1]heptan-3-one		C₆H₉NO	详情	详情
(II)	20474	ethyl 2-[(diethoxyphosphino)oxy]acetate		C₈H₁₇O₅P	详情	详情
(III)	20475	ethyl 2-(1-azabicyclo[2.2.1]hept-3-ylidene)acetate		C₁₀H₁₅NO₂	详情	详情
(IV)	16659	ethyl (2S)-2-hydroxypropanoate; (S)-ethyl lactate	687-47-8	C₅H₁₀O₃	详情	详情
(V)	20477	5'-Methyl-4'-oxospiro[1-azabicyclo[2,2,1]octane-3(S),2'-tetrahydrofuran]-3'-ylcarboxylic acid ethyl ester		C₁₃H₁₉NO₄	详情	详情

Extended Information