Methanol → [4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine (300 mg. 1.29 mmol) was dissolved in DCM (36 mL) and cooled to −50° C. A gentle flow of ozone was bubbled through the reaction mixture until the colour of the solution changed to slight blue. NaBH4 (486 mg. 12.9 mmol) dissolved in MeOH (15 mL) was added and the reaction was allowed to warm to RT over a period of 1 h. The solvents were removed in vacuo and the residue pardoned between water (20 mL) and EtOAc (20 mL) extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 40:1→20:1) to give the title compound. MS (m/z): 238.0 [M+H+].

Provenance & Evidence