tert-Butyl bromoacetate → (S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

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Reaction Steps

tert-Butyl 2-bromoacetate (1.358 g, 6.972 mmol) and tetra-n-butylammonium hydrogen sulfate (110 mg, 0.332 mmol) were stirred in sodium hydroxide solution (26 ml, 50% aq) and toluene (20 ml). A solution of (S)-(1-(4-methoxy-2,6-dimethyl-phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methanol (1.2 g, 3.32 mmol) in toluene (10 ml) was added slowly. The addition was exothermic, cooling was achieved with an ice bath. After stirring at room temperature for 1 h, the phases were separated and the aqueous phase was extracted with diethylether (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 5/1.

Provenance & Evidence