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【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