1-(3,4-dihydro-2-naphthalenyl)pyrrolidine -Drug Synthesis Database

【结构式】

【分子编号】20382

【品名】1-(3,4-dihydro-2-naphthalenyl)pyrrolidine

【CA登记号】21403-95-2

【分子式】C₁₄H₁₇N

【分子量】199.29572

【元素组成】C 84.37% H 8.6% N 7.03%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

The reaction of beta-tetralone (I) with pyrrolidine (A) yields enamine (II), which is condensed with phenacyl bromide (B) in DMF to give the 1-phenacyl-2-tetralone (III). Finally, this diketone is cyclized with 5-aminosalycilic acid (C) in refluxing acetic acid.

参考文献中间体

合成目标

【1】 Anderson, V.B.; et al.; Carboxyarylindoles as non steroidal anti-inflammatory agents. J Med Chem 1976, 1, 7, 320.
【2】 Castaner, J.; Arrigoni-Martelli, E.; Fendosal. Drugs Fut 1976, 1, 7, 320.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(A)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(I)	39106	3,4-Dihydro-2(1H)-naphthalenone; beta-Tetralone	530-93-8	C₁₀H₁₀O	详情	详情
(II)	20382	1-(3,4-dihydro-2-naphthalenyl)pyrrolidine	21403-95-2	C₁₄H₁₇N	详情	详情
(III)	40460	1-(2-oxo-2-phenylethyl)-3,4-dihydro-2(1H)-naphthalenone		C₁₈H₁₆O₂	详情	详情
(C)	29932	5-amino-2-hydroxybenzoic acid	89-57-6	C₇H₇NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The synthesis of Org-6370 is carried out in eight steps as follows: The 5,9-methanobenzocyclooctene system is prepared from tetralonepyrrolidine enamine (I) and acrolein (II), giving a mixture of the epimeric 8-alcohols (III), which are dehydroxylated via the intermediate p-toluenesulfonate esters. The unsaturated 11-ketone (IV) is converted by a reductive amination process using methylamine and sodium borohydride to an epimeric mixture of 11-methylamines. At this stage the epimeric amines are separated by crystallization and the required (11S*)-compound (V) is further methylated and converted to the hydrochloride.

参考文献中间体

合成目标

【1】 Timmer, C.J.; van der Waart, M.; Sam A.P.; Sitsen, J.M.A.; de Graaf, J.S.; Redpath, J.; ORG-6370. London: Libbey (B.S. Meldrum and R.J. Porter (Eds.) 1986.
【2】 Pento, J.T.; ORG-6370. Drugs Fut 1989, 14, 2, 130.

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)	20382	1-(3,4-dihydro-2-naphthalenyl)pyrrolidine	21403-95-2	C₁₄H₁₇N	详情	详情
(II)	17668	acrylaldehyde; Acrolein	107-02-8	C₃H₄O	详情	详情
(III)	20384	10-hydroxytricyclo[7.3.1.0(2,7)]trideca-2,4,6-trien-13-one		C₁₃H₁₄O₂	详情	详情
(IV)	20385	tricyclo[7.3.1.0(2,7)]trideca-2,4,6-trien-13-one		C₁₃H₁₄O	详情	详情
(V)	20386	N-methyl-N-[(13S)tricyclo[7.3.1.0(2,7)]trideca-2,4,6,10-tetraen-13-yl]amine; (13S)-N-methyltricyclo[7.3.1.0(2,7)]trideca-2,4,6,10-tetraen-13-amine		C₁₄H₁₇N	详情	详情

Extended Information