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【结 构 式】

【分子编号】33874

【品名】1-[5-(benzyloxy)-6-(hydroxymethyl)-2-pyridinyl]-2-(tert-butylamino)-1-ethanol

【CA登记号】

【 分 子 式 】C19H26N2O3

【 分 子 量 】330.42712

【元素组成】C 69.06% H 7.93% N 8.48% O 14.53%

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:(VI)

The reaction of 3-hydroxypyridine (I) first with formaldehyde and NaOH in water, and then with benzyl bromide (A) in ethanol gives 3-benzyloxy-2,6-bis(hydroxymethyl)pyridine hydrochloride (II), which is oxidized with MnO2 in refluxing benzene yielding 2-hydroxmethyl-3-benzyloxy-6-pyridincarboxaldehyde (III). The condensation of (III) with tertbutylisonitrile (B) and acetic acid in refluxing CHCl3 affords N-tertbutyl-2-(5-benzyloxy-6-hydroxymethyl-2-pyridil)-2-acetoxyacetamide (IV), which is hydrolyzed with 12N HCl yielding N-tertbutyl-2-(5-benzyloxy-6-hydroxymethyl-2-pyridil)-2-hydroxyacetamide (V). The reduction of the amide group of (V) with diborane in THF gives 2-hydroxymethyl-3-benzyloxy-6-(1-hydroxy-2-tertbutylaminoethyl)pyridine (VI), which is finally debenzylated with H2 over Pd/C in methanol.

1 Barth, W.; 2-Hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-aminoethyl)pyridines. DE 2204195; FR 2125309; GB 1367668; GB 1367669; US 3700681; US 3763173 .
2 Castaner, J.; Thorpe, P.; Pirbuterol. Drugs Fut 1977, 2, 1, 60.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(B) 33871 pivalonitrile 630-18-2 C5H9N 详情 详情
(I) 12911 3-Hydroxypyridine; 3-Pyridinol 109-00-2 C5H5NO 详情 详情
(II) 33869 [3-(benzyloxy)-6-(hydroxymethyl)-2-pyridinyl]methanol C14H15NO3 详情 详情
(III) 33870 5-(benzyloxy)-6-(hydroxymethyl)-2-pyridinecarbaldehyde C14H13NO3 详情 详情
(IV) 33872 1-[5-(benzyloxy)-6-(hydroxymethyl)-2-pyridinyl]-2-(tert-butylamino)-2-oxoethyl acetate C21H26N2O5 详情 详情
(V) 33873 2-[5-(benzyloxy)-6-(hydroxymethyl)-2-pyridinyl]-N-(tert-butyl)-2-hydroxyacetamide C19H24N2O4 详情 详情
(VI) 33874 1-[5-(benzyloxy)-6-(hydroxymethyl)-2-pyridinyl]-2-(tert-butylamino)-1-ethanol C19H26N2O3 详情 详情
Extended Information