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【结 构 式】

【分子编号】20290

【品名】3-quinuclidinecarboxylic acid

【CA登记号】

【 分 子 式 】C8H13NO2

【 分 子 量 】155.19676

【元素组成】C 61.91% H 8.44% N 9.03% O 20.62%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The synthesis of EO 122 starts from quinuclidine-3-carboxylic acid (I), which is converted to the acid chloride (II) by oxalyl chloride. The addition of 2,6-dimethylaniline (III) to the acid chloride yields EO-122.

1 Kaplinsky, E.; Bruckstein, R.; Kariv, E.; Oppenheimer, E.; Cohen, S.; A preclinical study of EO-122, a new lidocaine-lik. Angiology 1980, 31, 410.
2 Renk, E.; Grob, C.A.; Studie in the quinudidine line. 3-Quinudialine-car. Helv Chim Acta 1954, 37, 1689.
3 Oppenheimer, E.; Binah, O.; EO-122. Drugs Fut 1988, 13, 8, 724.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(I) 20290 3-quinuclidinecarboxylic acid C8H13NO2 详情 详情
(II) 20291 3-quinuclidinecarbonyl chloride C8H12ClNO 详情 详情
(III) 17527 2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine 87-62-7 C8H11N 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

A new synthesis of sabcomeline hydrochloride has been described: The hydrolysis of quinuclidine-3-carboxylic acid ethyl ester (I) with refluxing aqueous HCl gives the corresponding acid (II), which by reaction with thionyl chloride in refluxing dichloromethane yields the expected acyl chloride (III). The reaction of (III) with O-methylhydroxylamine in chloroform/pyridine affords N-methoxyquinuclidine-3-carboxamide (IV), which by reaction with triphenylphosphine/CCl4 in refluxing acetonirile is converted into the imidoyl chloride (V). The reaction of (V) with NaCN in hot DMSO gives 2-(methoxyimino)-2-(3-quinuclidinyl)acetonitrile (VI) as a mixture of the (E)- and (Z)-isomers that is resolved by column chromatography yielding the (Z)-isomer (VII). Finally, this compound (VII) is submitted to optical resolution with (R)-(-)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate [(R)-(-)-BNHP].

1 Bromidge, S.M.; Brown, F.; Cassidy, F.; et al.; Design of [R-(Z)]-(+)-alpha-(methoxyimino)-1-azabicyclo[2.2.2]octane-3-acetonitrile (SB 202026), a functionally selective azabicyclic muscarinic M1 agonist incorporating the N-methoxy imidoyl nitrile group as a novel ester bioisostere. J Med Chem 1997, 40, 26, 4265.
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) 20289 ethyl 3-quinuclidinecarboxylate; 3-carbethoxyquinuclidine; 1-azabicyclo[2.2.2]octane-3-ethylcarboxylate 6238-33-1 C10H17NO2 详情 详情
(II) 20290 3-quinuclidinecarboxylic acid C8H13NO2 详情 详情
(III) 20291 3-quinuclidinecarbonyl chloride C8H12ClNO 详情 详情
(IV) 16921 N-methoxy-3-quinuclidinecarboxamide C9H16N2O2 详情 详情
(V) 16922 N-methoxy-3-quinuclidinecarboximidoyl chloride C9H15ClN2O 详情 详情
(VII) 16923 N-methoxy-3-quinuclidinecarboximidoyl cyanide C10H15N3O 详情 详情
Extended Information