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【结 构 式】

【分子编号】19509

【品名】(2S)-1-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid

【CA登记号】

【 分 子 式 】C14H15NO4

【 分 子 量 】261.27744

【元素组成】C 64.36% H 5.79% N 5.36% O 24.49%

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:(XIII)

Compound (XII) is protected with benzyl chloroformiate (VII) to afford compound (XIII), which is condensed with 2,5-dimethylaniline (XIV) by means SOCl2/DMAP to yield amide (XIV). This compound (XIV) is deprotected by means trimethylsillyl chloride to yield compound (XV), which is hydrogenated by means Rh/Al2O3. Finally, this compound (V) is alkylated with 1-iodopropane by means potassium carbonate (K2CO3) to yield Ropivacaine.

1 T. af Ekenstam, B.; Bovin, C. (Alpharma Inc.); L-N-n-Propylpipecolic acid-2,6-xylidide and method for preparing the same. JP 1985502054; WO 8500599 .
2 Sandeberg, R.V. (AstraZeneca plc); S-(-)-1-propyl-2',6'-pipecoloxylidide hydrochloride monohydrate, process for its preparation and pharmaceutical preparation containing it. EP 0239710; US 4870086 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
28758 1-iodopropane 107-08-4 C3H7I 详情 详情
(IV) 17527 2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine 87-62-7 C8H11N 详情 详情
(V) 17531 (2S)-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide C14H20N2O 详情 详情
(VII) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(XII) 19508 (2S)-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid C6H9NO2 详情 详情
(XIII) 19509 (2S)-1-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid C14H15NO4 详情 详情
(XIV) 19510 benzyl (2S)-2-[(2,6-dimethylanilino)carbonyl]-3,4-dihydro-1(2H)-pyridinecarboxylate C22H24N2O3 详情 详情
(XV) 19511 (2S)-N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydro-2-pyridinecarboxamide C14H18N2O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XIII)

3) The protection of 1,2,3,6-tetrahydropyridine-2(S)-carboxylic acid (XII) with benzyl chloroformate (VII) gives the benzyloxycarbonyl derivative (XIII), which is condensed with 2,6-xylidine (IV) with SOCl2 and DMAP as before yielding the amide (XIV). Deprotection of (XIV) with iodotrimethylsilane in dichloromethane affords N-(2,6-dimethylphenyl)-1,2,3,6-tetrahydropyridine-2(S)-carboxamide (XV), which is reduced with H2 over Rh/Al2O3 in DMF giving the saturated amide (V). Finally, this compound is alkylated with propyl iodide and K2CO3 as before.

1 Prous, J.; Castaner, J.; ROPIVACAINE HYDROCHLORIDE < Rec INNM >. Drugs Fut 1989, 14, 8, 767.
2 Gawell, L.; Synthesis of tritium labelled ropivacaine - A new potential local anaesthetic. J Label Compd Radiopharm 1987, 24, 5, 521.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 17527 2,6-Xylidine; 2,6-Dimethylaniline; 2,6-Dimethylphenylamine 87-62-7 C8H11N 详情 详情
(V) 17531 (2S)-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide C14H20N2O 详情 详情
(VI) 19502 Propyl bromide; 1-Bromopropane 106-94-5 C3H7Br 详情 详情
(VII) 10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(XII) 19508 (2S)-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid C6H9NO2 详情 详情
(XIII) 19509 (2S)-1-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid C14H15NO4 详情 详情
(XIV) 19510 benzyl (2S)-2-[(2,6-dimethylanilino)carbonyl]-3,4-dihydro-1(2H)-pyridinecarboxylate C22H24N2O3 详情 详情
(XV) 19511 (2S)-N-(2,6-dimethylphenyl)-1,2,3,4-tetrahydro-2-pyridinecarboxamide C14H18N2O 详情 详情
Extended Information