【结 构 式】 |
【分子编号】51398 【品名】tetrahydro-1H-pyrrolizine-7a(5H)-carbonitrile 【CA登记号】 |
【 分 子 式 】C8H12N2 【 分 子 量 】136.19676 【元素组成】C 70.55% H 8.88% N 20.57% |
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 bicyclic nitrile (III) was prepared by reaction of 1,7-dichloroheptan-4-one (I) with 2-aminoisobutyronitrile (II) in the presence of methanolic ammonia (1). Addition of 2-adamantyllithium (IV) to nitrile (III) in Et2O at -50 C furnished ketone (V). Subsequent addition of 4-fluorophenylmagnesium bromide (VI) to ketone (V) in cold THF provided the desired carbinol, which was isolated as the corresponding hydrochloride salt by lyophilization of its solution in aqueous HCl.
【1】 Oka, M.; et al.; Synthesis and anti-influenza virus activity of tricyclic compounds with a unique amine moiety. Chem Pharm Bull 2001, 49, 4, 379. |
【2】 Kurono, M.; Baba, Y.; Oka, M.; Honda, N.; Matsumoto, Y.; Kakigami, T.; Iwata, N.; Ishiwata, Y.; Ohtuka, T.; Mitani, T.; Sawai, K. (Sanwa Kagaku Kenkyusho Co., Ltd.); Antivirally active N-cycloalkyl alkanol cpds.. EP 0558321; JP 1994048997 . |
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) | 19913 | 1,7-dichloro-4-heptanone | 40624-07-5 | C7H12Cl2O | 详情 | 详情 |
(II) | 18745 | 2-amino-2-methylpropanenitrile | 19355-69-2 | C4H8N2 | 详情 | 详情 |
(III) | 51398 | tetrahydro-1H-pyrrolizine-7a(5H)-carbonitrile | C8H12N2 | 详情 | 详情 | |
(IV) | 51399 | 2-adamantyllithium | C10H15Li | 详情 | 详情 | |
(V) | 51400 | 2-adamantyl[tetrahydro-1H-pyrrolizin-7(5H)-yl]methanone | C18H27NO | 详情 | 详情 | |
(VI) | 13643 | 4-fluorophenyl magnesium bromide;Bromo(4-fluorophenyl)magnesium;bromo(p-fluorophenyl)Magnesium;p-Fluorophenylmagnesium bromide | 352-13-6 | C6H4BrFMg | 详情 | 详情 |
Extended Information