Triethylamine → (S)-{1-[3-(2-methyl-morpholin-4-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

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Reaction Steps

The solution of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (4.36 g, 14.5 mmol), 2-Methyl-morpholine hydrochloric acid salt (4 g. 2eq.), palladium acetate (20 mol %, 652 mg), 2-(di-t-butylphosphino) biphenyl (40 mol %, 1.73 g), triethylamine (4.45 ml, 2.2eq.), and sodium tert-butoxide (1.54 g, 1.1eq) in toluene (26 ml) was stirred at 80° C. for 2 days. The solution was filtered through Celite Pad and washed with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate solution and the organic layer was separated. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography with 25% ethyl acetate/hexane. Yellow sticky oil was obtained as the product (2.7 g, 58% yield).

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