Sodium Hydroxide → tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate

Participants

Reaction Conditions

Reaction Steps

n-Bu4NCl (7.52 g, 27.1 mmol) was added to a solution of (1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (27.2 g, max. 73.8 mmol) in toluene/MC (150 ml/150 ml) and the mixture was cooled to 0° C. A 35% strength aqueous NaOH solution (300 ml) was then added. Bromoacetic acid tert-butyl ester (17.8 ml, 122 mmol) was then added dropwise to the reaction mixture and the mixture was stirred at room temperature for 3 hours. The organic phase was separated off, washed with water (3×300 ml), dried over Na2SO4 and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 3:1). The yield was 26.8 g (85% over 2 stages).

Provenance & Evidence