Sodium Methoxide → {1-[2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

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Reaction Steps

Crude 15 (8.2 g, 19.27 mmol) is treated with NaOMe (0.5M in methanol, 77 ml, 38.5 mmol) and heated under reflux for 24 hours. The solvent is then evaporated, the residue taken up in DCM and extracted with 1N—NaOH and brine. Drying and evaporation gave a brown oil which is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (from 1% to 5%).

Provenance & Evidence