2,6-Dimethylmorpholine, cis- → (s)-{1-[3-(cis-2,6-Dimethylmorpholin-4-yl)phenyl]ethyl}-carbamic acid tert-butyl ester

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A solution of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5 g, 16.7 mmol), cis-2,6-dimethylmorpholine (5.75 g, 3eq.), palladium acetate (5 mol %, 187 mg), 2-(di-t-butylphosphino) biphenyl (10 mol %, 498 mg), and sodium tert-butoxide (1.68 g, 1.05eq) in toluene (33 ml) was stirred at 80° C. for 1.5 hours. The solution was filtered through Celite Pad and washed with ethyl acetate. The filtrate was concentrated under vacuum and purified by flash chromatography with gradient of 20% ethyl acetate/hexane to 30% ethyl acetate/hexane over 20 minutes. The product was obtained as a yellow solid (2.12 g, 38% yield).

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