Reacción #48672

Ecuación de reacción

ethyl acetate

((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester

1,1-diphenylethylene

N-iodosuccinimide

→

desired compound

[(S)-2-benzyloxy-1-(2-iodo-1,1-diphenylethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowash with saturated aqueous sodium chloride
2. 2
   SecadoDry (magnesium sulfate)
3. 3
   Filtraciónfilter
4. 4
   Concentraciónconcentrate
5. 5
   OtroPurify on silica gel
6. 6
   Lavadoeluting with 0:100 to 30:70 ethyl acetate

Procedimiento

Dissolve ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (1.0 g, 3.55 mmol) and 1,1-diphenylethylene (0.534 g, 2.96 mmol) in acetonitrile (20 mL). Add N-iodosuccinimide (0.800 g, 3.55 mmol) and stir at room temperature 72 hours. Pour into ethyl acetate and wash with saturated aqueous sodium chloride. Dry (magnesium sulfate), filter and concentrate. Purify on silica gel, eluting with 0:100 to 30:70 ethyl acetate:hexanes to give the desired compound.

Fuente