tert-butyl 3-(iodomethyl)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】51120

【品名】tert-butyl 3-(iodomethyl)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₁₁H₂₀INO₂

【分子量】325.18981

【元素组成】C 40.63% H 6.2% I 39.02% N 4.31% O 9.84%

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)

Ethyl nipecotate (I) was protected as the N-Boc derivative (II) and subsequently reduced to alcohol (III) by means of LiAlH4. Conversion of alcohol (III) into iodide (IV) was achieved by treatment with iodine and triphenylphosphine. The dianion of the chiral azetidinecarboxylic acid (V) was alkylated with iodide (IV) to furnish adduct (VI) as a diastereomeric mixture that was desilylated to (VII) using tetrabutylammonium fluoride. Benzyl ester (VIII) was then obtained by reaction of carboxylic acid (VII) with benzyl bromide and NaHCO3.

参考文献中间体

合成目标

【1】 Treuner, U.; Kronenthal, D.R.; Xu, Z.; Seiler, S.; Slusarchyk, W.A.; Bisacchi, G.; Randazzo, M.E.; Sutton, J.C.; Shi, Z.; Zahler, R.; Schwinden, M.D. (Bristol-Myers Squibb Co.); Amidino and guanidino azetidinone tryptase inhibitors. WO 9967215 .

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)	25693	ethyl 3-piperidinecarboxylate	5006-62-2	C₈H₁₅NO₂	详情	详情
(II)	26186	1-(tert-butyl) 3-ethyl 1,3-piperidinedicarboxylate		C₁₃H₂₃NO₄	详情	详情
(III)	51124	tert-butyl 3-(hydroxymethyl)-1-piperidinecarboxylate		C₁₁H₂₁NO₃	详情	详情
(IV)	51120	tert-butyl 3-(iodomethyl)-1-piperidinecarboxylate		C₁₁H₂₀INO₂	详情	详情
(V)	51121	(2S,3R)-3-[[1-(tert-butoxycarbonyl)-3-piperidinyl]methyl]-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid		C₂₁H₃₈N₂O₅Si	详情	详情
(VI)	49426	(2S)-1-[tert-butyl(dimethyl)silyl]-4-oxo-2-azetidinecarboxylic acid		C₁₀H₁₉NO₃Si	详情	详情
(VII)	51122	(2S,3R)-3-[[1-(tert-butoxycarbonyl)-3-piperidinyl]methyl]-4-oxo-2-azetidinecarboxylic acid		C₁₅H₂₄N₂O₅	详情	详情
(VIII)	51123	tert-butyl 3-([(2S,3R)-2-[(benzyloxy)carbonyl]-4-oxoazetidinyl]methyl)-1-piperidinecarboxylate		C₂₂H₃₀N₂O₅	详情	详情

Extended Information