tert-butyl 5-oxo-4-(4-pentenyl)-1,4-diazepane-1-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】64400

【品名】tert-butyl 5-oxo-4-(4-pentenyl)-1,4-diazepane-1-carboxylate

【CA登记号】

【分子式】C₁₅H₂₆N₂O₃

【分子量】282.38312

【元素组成】C 63.8% H 9.28% N 9.92% O 17%

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)

Alkylation of 1-Boc-1,4-diazepine-5-one (I) with 5-bromo-1-pentene (II) in the presence of NaH provides the N-pentenyl diazepinone (III). Subsequent oxidative cleavage of the olefin double bond by means of NaIO4 in the presence of a catalytic amount of OsO4 furnishes aldehyde (IV). Alternatively, alkylation of diazepinone (I) with 4-bromo-1,1-dimethoxybutane (V) yields acetal (VI), which is further hydrolyzed to aldehyde (IV) in aqueous AcOH. Reductive amination of aldehyde (IV) with (S) N-propyl-2-(4-methanesulfonylphenyl)-1-methylethylamine (VII) leads to the tertiary amine (VIII). The N-Boc protecting group of (VIII) is finally cleaved by heating in 6 N HCl.

参考文献中间体

合成目标

【1】 Maag, H.; Fisher, L.E.; Prince, A.; Repke, D.B.; Dvorak, C.A.; Harris, R.N. III; Green, K.L.; Stabler, R.S. (F. Hoffmann-La Roche AG); Substd. 1-aminoalkyl-lactams and their use as muscarinic receptor antagonists. JP 2003534330; US 2002004501; US 6667301; WO 0190081 .

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)	64339	ethyl 3-(1-methyl-1H-pyrrol-2-yl)propanoate		C₁₀H₁₅NO₂	详情	详情
(II)	49724	1-Bromo-4-Pentene; 5-Bromo-1-pentene; 4-Penten-1-yl Bromide	1119-51-3	C₅H₉Br	详情	详情
(III)	64400	tert-butyl 5-oxo-4-(4-pentenyl)-1,4-diazepane-1-carboxylate		C₁₅H₂₆N₂O₃	详情	详情
(IV)	64401	tert-butyl 5-oxo-4-(4-oxobutyl)-1,4-diazepane-1-carboxylate		C₁₄H₂₄N₂O₄	详情	详情
(V)	64402	4-bromo-1,1-dimethoxybutane; 4-bromo-1-methoxybutyl methyl ether		C₆H₁₃BrO₂	详情	详情
(VI)	64403	tert-butyl 4-(4,4-dimethoxybutyl)-5-oxo-1,4-diazepane-1-carboxylate		C₁₆H₃₀N₂O₅	详情	详情
(VII)	64404	N-{(1S)-1-methyl-2-[4-(methylsulfonyl)phenyl]ethyl}-1-propanamine; N-{(1S)-1-methyl-2-[4-(methylsulfonyl)phenyl]ethyl}-N-propylamine		C₁₃H₂₁NO₂S	详情	详情
(VIII)	64405	tert-butyl 4-{4-[{(1S)-1-methyl-2-[4-(methylsulfonyl)phenyl]ethyl}(propyl)amino]butyl}-5-oxo-1,4-diazepane-1-carboxylate		C₂₇H₄₅N₃O₅S	详情	详情

Extended Information