1-Nitro-2-phenylethane → 2(S)-(2-Cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Add 1-phenyl-2-nitroethane (91 mg, 0.61 mmol) to a solution of 2-(S)-(2-cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester (164 mg, 0.50 mmol) in dry tetrahydrofuran (6 mL). Cool to 0° C. and add tetrabutylammonium fluoride (0.25 mL of a 1 M solution in tetrahydrofuran, 0.25 mmol) and refrigerate the solution overnight. Dilute with ethyl acetate, wash with cold saturated aqueous sodium chloride (50 mL), dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 2.5:97.5 ethyl acetate:dichloromethane) to give the desired compound as a white foam (152 mg, 63%).

Herkunft & Nachweise