tert-butyl 4-(5-methyl-4-phenyl-1H-pyrazol-1-yl)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】25310

【品名】tert-butyl 4-(5-methyl-4-phenyl-1H-pyrazol-1-yl)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₂₀H₂₇N₃O₂

【分子量】341.4534

【元素组成】C 70.35% H 7.97% N 12.31% O 9.37%

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：(IV)

N-Boc-4-Hydroxypiperidine (I) was converted to the mesylate (II) with methanesulfonyl chloride and pyridine. Then, alkylation of 3-methyl-4-phenylpyrazole (III) with (II) in the presence of NaH yielded a mixture of regioisomeric pyrazoles (IV) and (V), which were separated using flash chromatography. The required isomer (IV) was subsequently treated with HCl in Et2O to remove the Boc protecting group. The resulting piperidine (VI) was finally alkylated with 3-(bromomethyl)benzonitrile (VII) to afford the title compound.

参考文献中间体

合成目标

【1】 Bonner, K.; Jones, E.A.; Moore, K.W.; et al.; 4-N-Linked-heterocyclic piperidine derivatives with high affinity and selectivity for human dopamine D4 receptors. Bioorg Med Chem Lett 1999, 9, 9, 1285.

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)	18625	tert-butyl 4-hydroxy-1-piperidinecarboxylate		C₁₀H₁₉NO₃	详情	详情
(II)	25308	tert-butyl 4-[(methylsulfonyl)oxy]-1-piperidinecarboxylate		C₁₁H₂₁NO₅S	详情	详情
(III)	25309	3-methyl-4-phenyl-1H-pyrazole	3566-44-7	C₁₀H₁₀N₂	详情	详情
(IV)	25310	tert-butyl 4-(5-methyl-4-phenyl-1H-pyrazol-1-yl)-1-piperidinecarboxylate		C₂₀H₂₇N₃O₂	详情	详情
(V)	25311	tert-butyl 4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)-1-piperidinecarboxylate		C₂₀H₂₇N₃O₂	详情	详情
(VI)	25312	4-(5-methyl-4-phenyl-1H-pyrazol-1-yl)piperidine		C₁₅H₁₉N₃	详情	详情
(VII)	13244	alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile	28188-41-2	C₈H₆BrN	详情	详情

Extended Information