In 2013,Iwasaki, Takanori; Takagawa, Hiroaki; Singh, Surya P.; Kuniyasu, Hitoshi; Kambe, Nobuaki published 《Co-Catalyzed Cross-Coupling of Alkyl Halides with Tertiary Alkyl Grignard Reagents Using a 1,3-Butadiene Additive》.Journal of the American Chemical Society published the findings.Computed Properties of C7H15NO The information in the text is summarized as follows:
In the presence of cobalt(II) chloride, lithium iodide, and either 1,3-butadiene or isoprene, alkyl Grignard reagents with β-hydrogen atoms such as tert-butylmagnesium chloride underwent coupling reactions with alkyl tosylates, fluorides, bromides, and iodides such as 1-bromooctane in THF at 50° to give alkanes such as 2,2-dimethyldecane in 55-91% isolated yields or in 58-95% GC yields; sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. Ester-, amide-, and tetrahydropyran-containing alkyl bromides were compatible with the reaction conditions. Coupling reactions of 6-bromo-1-hexene and cyclopropylmethyl bromide did not yield cyclized product and gave low yields (<4%) of ring-opened products, resp., while reaction in the presence of 9,10-dihydroanthracene gave product in low yield but with complete recovery of dihydroanthracene, implying that the coupling does not occur through radical intermediates. An ionic mechanism with inversion of stereochem. at the reacting site of the alkyl halide is proposed for the coupling reaction based on the stereoselectivity of reaction of a racemic dideuterated phenethyl bromide. The experimental part of the paper was very detailed, including the reaction process of 2-(Piperidin-4-yl)ethanol(cas: 622-26-4Computed Properties of C7H15NO)
2-(Piperidin-4-yl)ethanol(cas: 622-26-4) can be used to synthese ursolic acid derivatives, spiroimidazolidinone NPC1L1 inhibitors, neurokinin-2 receptor antagonists, antagonists for inhibition of platelet aggregation.Computed Properties of C7H15NO
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem