Reacción #1869209

Ecuación de reacción

(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate

(3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol

Cs2CO3

→

subtitled compound

Rendimiento 14.3%

(3S)-1-({2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetyl)pyrrolidin-3-ol

Rendimiento 14.3%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was partitioned between ethyl acetate and H2O
2. 2
   SecadoThe organic layer was dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane)

Procedimiento

A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (228 mg, 0.88 mmol), (3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol (196 mg, 0.88 mmol) and Cs2CO3 (344 mg, 1.05 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography/(0-3% methanol in dichloromethane) to give the subtitled compound (35 mg).

Fuente