tert-butyl 6-chloro-2-ethoxy-4-methyl-3,4-dihydro-1(2H)-quinolinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】40944

【品名】tert-butyl 6-chloro-2-ethoxy-4-methyl-3,4-dihydro-1(2H)-quinolinecarboxylate

【CA登记号】

【分子式】C₁₇H₂₄ClNO₃

【分子量】325.8352

【元素组成】C 62.67% H 7.42% Cl 10.88% N 4.3% O 14.73%

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)

Lactam (I) was protected as the tert-butyl carbamate (II) by treatment with Boc2O in the presence of Et3N and DMAP. After reduction of (II) with NaBH4 in EtOH at -25 C, reaction with ethanolic HCl produced the ethoxy derivative (III). Treatment with TiCl4 in CH2Cl2 at -30 C generated the intermediate iminium salt (IV), that was converted into the target benzoquinolizinone system (VI) by the tandem Mannich-Michael condensation with 2-(trimethylsilyloxy)-1,3-butadiene (V). Finally, oxidation of (V) with mercuric acetate produced the desired unsaturated compound.

参考文献中间体

合成目标

【1】 Zorn, C.; Danza, G.; Mancina, R.; Serio, M.; Occhiato, E.G.; Scarpi, D.; Comerci, A.; Guarna, A.; Synthesis of 8-chloro-benzo[c]quinolizin-3-ones as potent and selective inhibitors of human steroid 5alpha-reductase 1. Bioorg Med Chem Lett 2000, 10, 4, 353.

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)	40942	6-chloro-4-methyl-3,4-dihydro-2(1H)-quinolinone		C₁₀H₁₀ClNO	详情	详情
(II)	40943	tert-butyl 6-chloro-4-methyl-2-oxo-3,4-dihydro-1(2H)-quinolinecarboxylate		C₁₅H₁₈ClNO₃	详情	详情
(III)	40944	tert-butyl 6-chloro-2-ethoxy-4-methyl-3,4-dihydro-1(2H)-quinolinecarboxylate		C₁₇H₂₄ClNO₃	详情	详情
(IV)	40945	1-(tert-butoxycarbonyl)-6-chloro-4-methyl-3,4-dihydroquinolinium		C₁₅H₁₉ClNO₂	详情	详情
(V)	18557	1-methylene-2-propenyl trimethylsilyl ether; trimethyl[(1-methylene-2-propenyl)oxy]silane	38053-91-7	C₇H₁₄OSi	详情	详情
(VI)	40946	8-chloro-6-methyl-1,2,4,4a,5,6-hexahydro-3H-pyrido[1,2-a]quinolin-3-one		C₁₄H₁₆ClNO	详情	详情

Extended Information