Reacción #48659

Ecuación de reacción

[(1R,2S,3S)-2-benzyloxy-3-dibenzylamino-4-(3,5-difluorophenyl)-1-hydroxymethyl-butyl]-((R)-3-cyclohexyloxy-2-hydroxypropyl)-carbamic acid tert-butyl ester

tributylphosphine

→

desired compound

Rendimiento 84.7%

(2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-cyclohexyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester

Rendimiento 84.7%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónfilter the slurry
2. 2
   Lavadowash with hexanes
3. 3
   Otropurify
4. 4
   Lavado(silica gel chromatography, eluting with 5:95 to 15:85 ethyl acetate:hexanes)

Procedimiento

Dissolve [(1R,2S,3S)-2-benzyloxy-3-dibenzylamino-4-(3,5-difluorophenyl)-1-hydroxymethyl-butyl]-((R)-3-cyclohexyloxy-2-hydroxypropyl)-carbamic acid tert-butyl ester (0.940 g, 1.216 mmol) in benzene (6 mL) followed by the addition of tributylphosphine (0.369 g, 1.824 mmol) and N,N-tetramethyl azodicarboxamide (TMAD) (0.314 g, 1.824 mmol). Stir vigorously for 16 hours, filter the slurry, wash with hexanes and purify (silica gel chromatography, eluting with 5:95 to 15:85 ethyl acetate:hexanes) to give the desired compound as a white foam (0.777 g, 84.7%).

Fuente