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【结 构 式】

【分子编号】12987

【品名】1-Propynyl-1-cyclohexanol; 1-(1-Propynyl)cyclohexanol

【CA登记号】697-37-0

【 分 子 式 】C9H14O

【 分 子 量 】138.20956

【元素组成】C 78.21% H 10.21% O 11.58%

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:(VII)

This compound can be obtained in a simple way: Under nitrogen, borontrifluoride etherate solution is added to heated 2-methyl-1-propanol (II), and 1-chloro-2,3-epoxypropane (I) is added. When the reaction is completed, pyrrolidine (IV) is added to obtain alpha-[2-methyl-propoxymethyl]-1-pyrrolidine-ethanol (V). 1-[2-Chloro-3-(2-methylpropoxy)propyl]pyrrolidine (VI) is obtained by chlorination with thionyl chloride of the subsequent amino alcohol. The condensation of 1-propynyl-1-cyclohexanol (VII) with 1-[2-chloro-3-(2-methylpropoxy)propyl]pyrrolidine (VI) in toluene and sodium hydroxide in water affords dopropidil. Due to the pyrrolidine shift mechanism, the reaction yields the correct structure, confirmed by 1H and 13C NMR as well as by mass spectra and X-ray analysis. The pyrrolidine shift mechanism is explained by the assumption of an intermediate aziridinium ion (VIII), which is opened regiospecifically at the less hindered C-N bond by the nucleophile ion.

1 Carlier, P.; Montell, A.J.-C.; Simond, J.A.L. (Riom Laboratoires); Ethers of 1-(2-propynyloxy)-2-amino-3-propanol, their preparation and their application in therapeutic. EP 0031771; US 4430332 .
2 Dupont, L.; Dideberg, O.; Simond, J.; X-ray analysis of CERM 4205. Acta Cryst Sect C 1986, 42, 864.
3 Massingham, R.; Monteil, A.; DOPROPIDIL HYDROCHLORIDE. Drugs Fut 1990, 15, 5, 453.
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) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(II) 12982 2-Methyl-1-propanol 78-83-1 C4H10O 详情 详情
(III) 12983 2-(Isobutoxymethyl)oxirane; Isobutyl 2-oxiranylmethyl ether C7H14O2 详情 详情
(IV) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(V) 12985 1-Isobutoxy-3-(1-pyrrolidinyl)-2-propanol C11H23NO2 详情 详情
(VI) 12986 2-Chloro-3-(1-pyrrolidinyl)propyl isobutyl ether; 1-(2-Chloro-3-isobutoxypropyl)pyrrolidine C11H22ClNO 详情 详情
(VII) 12987 1-Propynyl-1-cyclohexanol; 1-(1-Propynyl)cyclohexanol 697-37-0 C9H14O 详情 详情
(VIII) 12988 1-(Isobutoxymethyl)-3-azoniaspiro[2.4]heptane C11H22NO 详情 详情
Extended Information