• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】48405

【品名】1-(tert-butyl) 3-methyl 1,3-piperazinedicarboxylate

【CA登记号】

【 分 子 式 】C11H20N2O4

【 分 子 量 】244.29088

【元素组成】C 54.08% H 8.25% N 11.47% O 26.2%

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:(XII)

Piperazine-2-carboxylic acid (VIII) was prepared by catalytic hydrogenation of pyrazine (VII). Sequential protection of the N-4 of (VIII) with 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile and the N-1 with benzyl chloroformate provided the diprotected piperazinecarboxylic acid (X), which was subsequently esterified with diazomethane to give the methyl ester (XI). The N-benzyloxycarbonyl group of (XI) was selectively deprotected by hydrogenation in the presence of Pd/C to yield the N-Boc-piperazine (XII). Reductive alkylation of (XII) with isovaleraldehyde (XIII) afforded the corresponding N-isoamyl piperazine (XIV). After acid removal of the N-Boc group of (XIV) to yield (XV), a second reductive alkylation with acetone (XVI) produced the dialkyl piperazine (XVII). Hydrolysis of the methyl ester group of (XVII) under acidic conditions gave acid (XVIII). This was finally coupled with the intermediate piperidine (VI) in the presence of HBTU to provide the title compound.

1 Rafferty, M.F.; Hu, L.-Y.; Ryder, T.R.; et al.; Synthesis and biological activity of 4-aminopiperidine derivatives as N-type calcium channel antagonists. Med Chem Res 2000, 10, 1, 11.
2 Ryder, T.R.; Rafferty, M.F.; Hu, L.-Y. (Pfizer Inc.); Heterocyclic substd. aniline calcium channel blockers. US 6251919; WO 9943658 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 38232 N-[4-(benzyloxy)phenyl]-N-(3-methyl-2-butenyl)-N-(4-piperidinyl)amine; N-[4-(benzyloxy)phenyl]-N-(3-methyl-2-butenyl)-4-piperidinamine C23H30N2O 详情 详情
(VII) 37256 2-pyrazinecarboxylic acid; Pyrazinoic acid 98-97-5 C5H4N2O2 详情 详情
(VIII) 25933 2-piperazinecarboxylic acid; Piperazine-2-carboxylic acid C5H10N2O2 详情 详情
(IX) 25934 4-(tert-butoxycarbonyl)-2-piperazinecarboxylic acid C10H18N2O4 详情 详情
(X) 48403 N-4-Boc-N-1-CBz-2-piperazinecarboxylic acid; 1-[(benzyloxy)carbonyl]-4-(tert-butoxycarbonyl)-2-piperazinecarboxylic acid 129365-23-7 C18H24N2O6 详情 详情
(XI) 48404 1-benzyl 4-(tert-butyl) 2-methyl 1,2,4-piperazinetricarboxylate C19H26N2O6 详情 详情
(XII) 48405 1-(tert-butyl) 3-methyl 1,3-piperazinedicarboxylate C11H20N2O4 详情 详情
(XIII) 26052 3-methylbutanal 590-86-3 C5H10O 详情 详情
(XIV) 48406 1-(tert-butyl) 3-methyl 4-isopentyl-1,3-piperazinedicarboxylate C16H30N2O4 详情 详情
(XV) 48407 methyl 1-isopentyl-2-piperazinecarboxylate C11H22N2O2 详情 详情
(XVI) 23199 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one; Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether 67-64-1 C3H6O 详情 详情
(XVII) 48408 methyl 1-isopentyl-4-isopropyl-2-piperazinecarboxylate C14H28N2O2 详情 详情
(XVIII) 48409 1-isopentyl-4-isopropyl-2-piperazinecarboxylic acid C13H26N2O2 详情 详情
Extended Information