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【结 构 式】

【分子编号】42301

【品名】(1,5-diisopropyl-1H-pyrazol-3-yl)methanol

【CA登记号】

【 分 子 式 】C10H18N2O

【 分 子 量 】182.2658

【元素组成】C 65.9% H 9.95% N 15.37% O 8.78%

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)

Condensation of 3-methyl-2-butanone (I) with methyl 2-methoxyacetate (II) by means of sodium in toluene gave diketone (III). Pyrazole (IV) was prepared by treatment of diketone (III) with hydrazine. Subsequent alkylation of pyrazole (IV) with isopropyl iodide in the presence of sodium hydride provided a mixture of N-alkylated regioisomers (V) and (VI). The desired minor isomer (V) was demethylated with BBr3 and the resulting alcohol (VII) was oxidized to aldehyde (VIII) using manganese dioxide. Addition of vinylmagnesium bromide to the formyl group of (VIII) produced allylic alcohol (IX), which was further oxidized to ketone (X) with MnO2. The benzoin-type condensation of unsaturated ketone (X) with aldehyde (XI) in the presence of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride furnished the 1,4-diketone (XII). Cyclization of (XII) to pyrrole (XIII) was carried out by treatment with ammonium acetate in refluxing MeOH. Finally, ester hydrolysis by means of NaOH gave rise to the corresponding carboxylic acid.

1 Yamauchi, T.; Tokuhara, N.; Yoshimura, H.; Nagai, M.; Hida, T.; Tai, K.; Hibi, S.; Kikuchi, K.; Novel retinoic acid receptor alpha agonists: Syntheses and evaluation of pyrazole derivatives. Bioorg Med Chem Lett 2000, 10, 7, 619.
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) 26143 3-methyl-2-butanone 563-80-4 C5H10O 详情 详情
(II) 19100 methyl 2-methoxyacetate 6290-49-9 C4H8O3 详情 详情
(III) 42297 1-methoxy-5-methyl-2,4-hexanedione C8H14O3 详情 详情
(IV) 42298 (3-isopropyl-1H-pyrazol-5-yl)methyl methyl ether; 3-isopropyl-5-(methoxymethyl)-1H-pyrazole C8H14N2O 详情 详情
(V) 42299 1,5-diisopropyl-3-(methoxymethyl)-1H-pyrazole; (1,5-diisopropyl-1H-pyrazol-3-yl)methyl methyl ether C11H20N2O 详情 详情
(VI) 42300 1,3-diisopropyl-5-(methoxymethyl)-1H-pyrazole; (1,3-diisopropyl-1H-pyrazol-5-yl)methyl methyl ether C11H20N2O 详情 详情
(VII) 42301 (1,5-diisopropyl-1H-pyrazol-3-yl)methanol C10H18N2O 详情 详情
(VIII) 42302 1,5-diisopropyl-1H-pyrazole-3-carbaldehyde C10H16N2O 详情 详情
(IX) 42303 1-(1,5-diisopropyl-1H-pyrazol-3-yl)-2-propen-1-ol C12H20N2O 详情 详情
(X) 42304 1-(1,5-diisopropyl-1H-pyrazol-3-yl)-2-propen-1-one C12H18N2O 详情 详情
(XI) 10170 methyl 4-formylbenzoate 1571-08-0 C9H8O3 详情 详情
(XII) 42305 methyl 4-[4-(1,5-diisopropyl-1H-pyrazol-3-yl)-4-oxobutanoyl]benzoate C21H26N2O4 详情 详情
(XIII) 42306 methyl 4-[5-(1,5-diisopropyl-1H-pyrazol-3-yl)-1H-pyrrol-2-yl]benzoate C21H25N3O2 详情 详情
Extended Information