2-adamantyl[tetrahydro-1H-pyrrolizin-7(5H)-yl]methanone -Drug Synthesis Database

【结构式】

【分子编号】51400

【品名】2-adamantyl[tetrahydro-1H-pyrrolizin-7(5H)-yl]methanone

【CA登记号】

【分子式】C₁₈H₂₇NO

【分子量】273.41852

【元素组成】C 79.07% H 9.95% N 5.12% O 5.85%

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：(V)

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.

参考文献中间体

合成目标

【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