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【结 构 式】

【分子编号】36545

【品名】tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamate

【CA登记号】

【 分 子 式 】C18H28N2O3

【 分 子 量 】320.432

【元素组成】C 67.47% H 8.81% N 8.74% O 14.98%

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:(XVI)

4-(Aminomethyl)-1-benzyl-4-hydroxypiperidine (XV) was protected as the tert-butyl carbamate (XVI) and the benzyl group was subsequently cleaved by transfer hydrogenolysis employing ammonium formate and Pd/C yielding (XVII). Condensation of piperidine (XVII) with mesylate (VIII) in the presence of K2CO3 in boiling isopropanol furnished adduct (XVIII). After deprotection of the Boc group of (XVIII) with trifluoroacetic acid, reductive alkylation of the resulting amine (XIX) with benzaldehyde in the presence of NaBH3CN provided the N-benzyl amine (XX). Finally, a further reductive alkylation of (XX) with formaldehyde and NaBH3CN yielded the title compound.

1 Stanton, J.A.; Showell, G.A.; Neduvelil, J.G.; Bourrain, S.; Beer, M.S.; MacLeod, A.M.; 4-Hydroxy-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperidines: Selective h5-HT1D agonists for the treatment of migraine. Bioorg Med Chem Lett 1999, 9, 23, 3369.
2 Baker, R.; Bourrain, S.; Castro Pineiro, J.L.; Chambers, M.S.; Guiblin, A.R.; Hobbs, S.C.; Jelley, R.A.; Madin, A.; Matassa, V.G.; Reeve, A.J.; Russell, M.G.N.; Showell, G.A.; Sternfeld, F.; Street, L.J.; Van Niel, M.B. (Merck Sharp & Dohme Ltd.); Azetidine, pyrrolidine and piperidine derivs.. EP 0804434; JP 1998503768; US 5854268; WO 9604274 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(VIII) 36539 3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl methanesulfonate C14H16N4O3S 详情 详情
(XV) 36544 4-(aminomethyl)-1-benzyl-4-piperidinol C13H20N2O 详情 详情
(XVI) 36545 tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamate C18H28N2O3 详情 详情
(XVII) 36546 tert-butyl (4-hydroxy-4-piperidinyl)methylcarbamate C11H22N2O3 详情 详情
(XVIII) 36547 tert-butyl (4-hydroxy-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinyl)methylcarbamate C24H34N6O3 详情 详情
(XIX) 36548 4-(aminomethyl)-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinol C19H26N6O 详情 详情
(XX) 36549 4-[(benzylamino)methyl]-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinol C26H32N6O 详情 详情
Extended Information