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【结 构 式】

【分子编号】56549

【品名】benzyl 4-({4-[(tert-butoxycarbonyl)amino]-1-piperidinyl}methyl)-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C24H37N3O4

【 分 子 量 】431.5756

【元素组成】C 66.79% H 8.64% N 9.74% O 14.83%

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:(VI)

Isonipecotic acid (I) was protected with benzyl chloroformate and the resultant 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (II) was subsequently converted to the corresponding acid chloride (III) by treatment with SOCl2. Coupling of acid chloride (III) with 4-(tert-butoxycarbonylamino)piperidine (IV) afforded the piperidinyl amide (V), which was further reduced with BH3 to the piperidinylmethyl piperidine (VI). Aminopiperidine (VII), obtained by acidic cleavage of the N-Boc group of (VI), was then coupled with 4-amino-5-chloro-2-methoxybenzoic acid (VIII) to provide amide (IX). Deprotection of the N-benzyloxycarbonyl group was carried out by means of methanesulfonic acid in the presence of anisole to give (X). Acylation of piperidine (X) with the protected aminoacid (XI) yielded amide (XII). Then, selective reduction of the aliphatic amide function, followed by deprotection of the amino group provided the title compound.

1 Harada, H.; et al.; Novel N-[1-(1-substituted 4-piperidinylmethyl)-4-piperidinyl]benzamides as potent colonic prokinetic agents. Bioorg Med Chem Lett 2002, 12, 6, 967.
2 Kato, S.; Yoshida, N.; Harada, H.; Toyotomi, Y.; Morikage, S. (Dainippon Pharmaceutical Co., Ltd.); Benzamido derivs. and medicinal compsns. containing the same. JP 1999001472 .
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) 17462 (6S)-6-[(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]-5,6-dihydro-2H-pyran-2-one C25H20FNO2 详情 详情
(II) 56082 Z-Isonipecotic acid 10314-98-4 C14H17NO4 详情 详情
(III) 35165 benzyl 4-(chlorocarbonyl)-1-piperidinecarboxylate C14H16ClNO3 详情 详情
(IV) 41601 tert-butyl 4-piperidinylcarbamate; 4-tert-Boc-aminopiperidine 73874-95-0 C10H20N2O2 详情 详情
(V) 56548 benzyl 4-({4-[(tert-butoxycarbonyl)amino]-1-piperidinyl}carbonyl)-1-piperidinecarboxylate C24H35N3O5 详情 详情
(VI) 56549 benzyl 4-({4-[(tert-butoxycarbonyl)amino]-1-piperidinyl}methyl)-1-piperidinecarboxylate C24H37N3O4 详情 详情
(VII) 56550 benzyl 4-[(4-amino-1-piperidinyl)methyl]-1-piperidinecarboxylate C19H29N3O2 详情 详情
(VIII) 12419 4-Amino-5-chloro-2-methoxybenzoic acid 7206-70-4 C8H8ClNO3 详情 详情
(IX) 56551 benzyl 4-({4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidinyl}methyl)-1-piperidinecarboxylate C27H35ClN4O4 详情 详情
(X) 56552 4-amino-5-chloro-2-methoxy-N-[1-(4-piperidinylmethyl)-4-piperidinyl]benzamide C19H29ClN4O2 详情 详情
(XI) 56553 N-Carbobenzoxy-4-amino-n-butyric acid; N-Carbobenzoxy-gamma-aminobutyric acid 5105-78-2 C12H15NO4 详情 详情
(XII) 56554 benzyl 4-[4-({4-[(4-amino-5-chloro-2-methoxybenzoyl)amino]-1-piperidinyl}methyl)-1-piperidinyl]-4-oxobutylcarbamate C31H42ClN5O5 详情 详情
Extended Information