4-methyl-1-[2-[(2R)pyrrolidinyl]ethyl]piperidine -Drug Synthesis Database

【结构式】

【分子编号】23315

【品名】4-methyl-1-[2-[(2R)pyrrolidinyl]ethyl]piperidine

【CA登记号】

【分子式】C₁₂H₂₄N₂

【分子量】196.33604

【元素组成】C 73.41% H 12.32% N 14.27%

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：(VII)

Treatment of (R)-2-pyrrolidine methanol (I) with di-tert-butyl dicarbonate and K2CO3 gave carbamate (II), which was converted to mesylate (III) using methanesulfonyl chloride and Et3N. Subsequent reaction of (III) with NaCN in DMF provided nitrile (IV). The catalytic hydrogenation of this nitrile in the presence of 4-methylpiperidine (V) furnished the (piperidinylethyl)pyrrolidine (VI). After Boc deprotection of (VI) with trifluoroacetic acid in refluxing CH2Cl2, the resulting pyrrolidine (VII) was finally condensed with m-toluenesulfonyl chloride (VIII) to give the target sulfonamide.

参考文献中间体

合成目标

【1】 King, F.D.; Forbes, I.T.; Rahman, S.K. (SmithKline Beecham plc); Sulphonamide derivs. and their use in the treatment of CNS disorders. WO 9748681 .

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)	23309	(2R)pyrrolidinylmethanol	68832-13-3	C₅H₁₁NO	详情	详情
(II)	23310	tert-butyl (2R)-2-(hydroxymethyl)-1-pyrrolidinecarboxylate		C₁₀H₁₉NO₃	详情	详情
(III)	23311	tert-butyl (2R)-2-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylate		C₁₁H₂₁NO₅S	详情	详情
(IV)	23312	tert-butyl (2R)-2-(cyanomethyl)-1-pyrrolidinecarboxylate		C₁₁H₁₈N₂O₂	详情	详情
(V)	10192	4-Methylpiperidine; gamma-Pipecoline	626-58-4	C₆H₁₃N	详情	详情
(VI)	23314	tert-butyl (2R)-2-[2-(4-methyl-1-piperidinyl)ethyl]-1-pyrrolidinecarboxylate		C₁₇H₃₂N₂O₂	详情	详情
(VII)	23315	4-methyl-1-[2-[(2R)pyrrolidinyl]ethyl]piperidine		C₁₂H₂₄N₂	详情	详情
(VIII)	23316	3-methylbenzenesulfonyl chloride	1899-93-0	C₇H₇ClO₂S	详情	详情

Extended Information