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【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.

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