CAS: 102518-79-6; (5R,9R,E)-5-Amino-11-Ethylidene-7-Methyl-5,6,9,10-Tetrahydro-5,9-Methanocycloocta[b]Pyridin-2(1H)-One

上下游产品

2,7]trideca-2(7),3,5,10-tetraene-1-carboxylic acid(1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraene-1-carboxylic acid methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methan°Cyclo°Cta[b]pyridin-5-yl)carbamate (5S,9R)-methyl 2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methano-cyclo°Cta[b]pyridine-5-carboxylate 2,7]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester(1S,9S)-5-Methoxy-11-methylene-13-oxo-6-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-1-carboxylic acid methyl ester (5R,9R,11E)-5-(4-hydroxy-3-methoxyphenylmethylidenylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methan°Cyclo°Cta[b]pyridin-2(1H)-one (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methan°Cyclo°Cta[b]pyridin-2(1H)-one

(1R,9R)-13-Eth-(E)-Ylidene-5-Methoxy-11-Methyl-6-Aza-Tricyclo[7.3.1.02,7]Trideca-2(7),3,5,10-Tetraene-1-Carboxylic Acid Methyl Ester置于甲醇,Sodium Hydroxide,碘代三甲硅烷,二苯基膦叠氮化物,三乙胺体系中,用 四氢呋喃,甲醇,水 用作溶剂,化学反应 90.0H,反应生成石杉碱甲
参考文献:石杉碱甲及其氟化类似物的合成研究.1.石杉碱甲对映体对的新型不对称合成
标题:石杉碱甲及其氟化类似物的合成研究.1.石杉碱甲对映体对的新型不对称合成
摘要:石杉碱甲的对映异构体对的合成是通过两种方法完成的,该方法采用串联金鸡纳生物碱促进β-酮酸酯3与甲基丙烯醛的不对称迈克尔加成/醛醇缩合反应(4)(最大64%ee,3) + 4->5,方案2)和3的不对称双环环化反应与2-手性二茂铁基膦配体的钯催化剂催化的2-乙酸-1,3-丙二醇二乙酸酯(7)(最大64%ee,3 + 7->8,方案) 3)作为关键步骤.部分旋光的三环(+)-和(-)-6的重结晶衍生自不对称反应产物的化合物,很容易提供相应的光学纯样品(均> 99%ee).根据报道的方法,对映异构体对的全合成1-[(-)-和(+)-1 ]完成与光学纯(+)起始-和(-)-6(方案4).
Doi:10.1016/s0040-4020(98)00227-0

专利信息

专利号:US-6271379-B1
优先权日:2000-03-08
标题:Intermediates useful for the synthesis of huperzine A
发明人：TUECKMANTEL WERNER; KOZIKOWSKI ALAN P
权利人:UNIV GEORGETOWN
摘要:Intermediates useful for the synthesis of huperzine A represented by the structures below, n and methods for their synthesis, wherein: n R 1 is lower alkyl, benzyl, or substituted benzyl; n X is a suitable leaving group; n Y is an electron withdrawing group that can subsequently be converted into an amino group; n one broken line is present as a carbon—carbon bond and the other broken line is absent, where the broken line forms an unconjugated carbon—carbon double bond, which double bond may be endocyclic whereby n is 3 or the double bond may be exocyclic whereby n is 2.

专利号:US-2003083352-A1
优先权日:2000-07-31
标 题 :Synthesis of imidazole intermediates
发明人：HELAL CHRISTOPHER J
权利人:PFIZER
摘要:The invention provides a method for synthesis of compounds of formula n n n wherein R 1 and R 19 are as defined. Compounds of formula 12 are useful as intermediates for synthesizing compounds having pharmacological activity inhibiting cdk5, cdk2, and GSK-3.

专利号:US-4929731-A
优先权日:1989-02-21
标题:Method for the synthesis of huperzine A and analogs thereof and compounds useful therein
发明人：KOZIKOWSKI ALAN P; XIA YAN
权利人:UNIV PITTSBURGH
摘要:The present invention relates to a method for the synthesis of certain bridged fused ring pyridines. Such bridged fused ring pyridines can be converted to huperzine A and analogs of huperzine A. The present invention also covers such bridged fused ring pyridines, compounds utilized for the preparation of the bridged fused ring pyridines and analogs of huperzine A.

专利号:US-2009247754-A1
优先权日:2008-03-25
标 题:Method of preparing huperzine a and derivatives thereof
发明人：UNDERINER GAIL; GIBSON FRANK; HE LINLI; MEERA HARIHARA SUBRAMANIAN; GNANADEEPAM JESUDOSS MERCY; SAIGANESH RAMANATHAN; TUDHOPE STEPHEN R; AZADI-ARDAKANI MANOUCHEHR
权利人:DEBIOPHARM SA
摘要:The present invention is related to the synthesis of huperzine A. The synthesis includes a variety of process steps that increase productivity, reduce safety concerns, and allow for increasing production of compounds of desired optical isomer. The inventive methods may encompass a single improved reaction step that may be incorporated into a known reaction process for synthesizing huperzine A or a derivative thereof to improve the overall reaction. The inventive methods also encompass complete synthesis methods for preparing huperzine A or a derivative thereof.

专利号:US-8063062-B2
优先权日:2006-12-20
标 题 :Compounds with a combination of cannabinoid-CB1 antagonism and acetylcholinesterase inhibition
发明人：LANGE JOSEPHUS H M; KRUSE CORNELIS G; SHADID BELAL
权利人:LANGE JOSEPHUS H M; KRUSE CORNELIS G; SHADID BELAL; SOLVAY PHARM BV
摘要:Embodiments of this invention relate to compounds having a combination of cannabinoid-CB 1 antagonism and cholinesterase inhibition, to pharmaceutical compositions comprising these compounds, to methods for preparing these compounds, methods for preparing novel intermediates useful for the synthesis of these compounds, and methods for preparing compositions comprising these compounds. The invention also relates to methods of treating Alzheimer's disease, cognitive disorders, memory disorders, dementia, attention deficit disorder, traumatic brain injury, drug dependence, addiction or substance abuse by administering a pharmaceutical composition comprising these compounds to a patient in need thereof. A compound with a combination of cannabinoid-CB 1 antagonism and cholinesterase inhibition is a compound of formula (1) n nwherein the symbols have the meanings given in the specification.

专利号:US-7309799-B2
优先权日:2004-06-01
标 题:Methods for the synthesis of milnacipran and congeners thereof
发明人：BUCHWALD STEPHEN L; SWAGER TIMOTHY M; RARIY ROMAN V
权利人:COLLEGIUM PHARMACEUTICAL INC
摘要:One aspect of the present invention relates to methods for synthesizing milnacipran or congeners thereof. Another aspect of the present invention relates to asymmetric methods for synthesizing enantiomerically enriched milnacipran or congeners thereof. The present invention also relates to methods for synthesizing intermediates useful in the non-asymmetric or asymmetric methods for synthesizing enantiomerically enriched milnacipran or congeners thereof.