Water → methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)pyridine-1(2H)-carboxylate

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Reaction Conditions

Reaction Steps

4-((tert-Butyldimethylsilyloxy)methyl)pyridine (5.58 g, 25 mmol) (from reference compound 4, step 1) was dissolved in dry THF (50 mL) under nitrogen and the mixture cooled to −15° C. (3,3-Dimethylbutyl)magnesium chloride (0.5 M in THF) (50 mL, 25 mmol) was added dropwise during 20 min to yield a yellow solution which was stirred at −15° C. for 30 min. Then, methyl carbonochloridate (2.5 mL, 32 mmol) was added during 1 min. The reaction was continued at −15° C. for 30 min and then the mixture was cooled to −60° C. After 2 h the temperature had reached room temperature. Water (20 mL) was added and the solvent evaporated. The aqueous phase was extracted with DCM (×2) and the combined organic phase passed through a phase separator. The solvent was evaporated to yield a yellow oil. The residue was purified via Biotage (0=>10% EtOAc in heptane) to yield methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)pyridine-1(2H)-carboxylate (3.67 g, 44%) as a colourless oil. MS m/z 368 (M+H)+

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