Description
4-Aminotetrahydropyran contains the tetrahydropyran ring, which is the most frequently reported three-dimensional ring system in marketed drugs, and is second only to the phenyl ring when two-dimensional rings are included. It can be used as reactant/reagent in synthesis of aminothiazole compounds for use in treatment of cancer. Its scaffold is very useful in the drug discovery for cancer treatment.
Synthesis
General procedure for the synthesis of 4-aminotetrahydropyran from dihydro-2H-pyran-4(3H)-one oxime: Raney Ni (10%) was added to a stirred solution of compound 2.2 (1.0 g, 8.7 mmol) in methanol (50 mL) and the resulting mixture was stirred for 5 hr at room temperature in a hydrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the catalyst was removed by filtration and the methanol solvent in the filtrate was concentrated in vacuum to afford the target product 4-aminotetrahydropyran (Compound 2.3, 0.5 g, 57% yield).
References
[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2210 - 2221
[2] Patent: US2009/82423, 2009, A1. Location in patent: Page/Page column 23
[3] Patent: US5707989, 1998, A
[4] Patent: US5821240, 1998, A
[5] Patent: US5977102, 1999, A
