(2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester → (2R,3S,5R)-5-[(1S,2S)-1-Hydroxy-2-acetylamino-3-(3-propyl-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester

참여 물질

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반응 단계

Add propyl zinc bromide (2.311 g) in tetrahydrofuran and (1,1′-bis(diphenylphosphino)ferrocene) palladium(II) chloride (0.015 g) to a solution of (2R,3S,5R)-5-[(1S,2S)-1-hydroxy-2-acetylamino-3-(3-bromo-5-fluorophenyl)-propyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (0.07 g, 0.122 mmol) in tetrahydrofuran (1.2 mL) in a sealed tube flushed with nitrogen. Heat the tube at 65° C. for 6.5 hours. Add saturated aqueous ammonium chloride (5 mL). Extract the reaction mixture with ethyl acetate (2×30 mL). Combine the organic phases and wash with saturated aqueous sodium chloride (1×15 mL), dry over magnesium sulfate and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with hexanes containing 15-45% ethyl acetate, to provide 0.039 g (60%) of the title compound as an off-white foam.

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