Hydrogen Peroxide → [2-(dimethylamino)-3-pyridinyl]methanol(SALTDATA: HCl)

Participants

Reaction Conditions

Reaction Steps

To a cold (ca. -78° C.) solution of 2.9 g (21 mMol) of 3-methyl-2-(N,N-dimethylamino)pyridine in 35 ml of tetrahydrofuran was added dropwise 15 ml (23 mMol) of 1.55 M butyllithium in hexane. The mixture was stirred at 0° C. for four hours and then recooled to ca. -78° C. Trimethyl borate (2.65 ml, ca. 23 mMol) was added dropwise and the mixture was stirred at 0° C. After one hour 2.9 ml of 30% hydrogen peroxide was added and the mixture was stirred at 25° C. After another hour, the reaction mixture was poured into water and extracted with several portions of diethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel (using ethanol-toluene as eluent) yielded 600 mg of 3-hydroxymethyl-2-(N,N-dimethylamino)pyridine, as confirmed by the nmr and infrared spectra. Using the method of Example 79 with 3-hydroxymethyl-2-(N,N-dimethylamino) pyridinamine instead of 3-hydroxymethyl-2-pyridinamine yielded the title compound, which was used in subsequent reactions without further purification. Structure assignment was supported by the nmr and infrared spectra.

Provenance & Evidence