Reacción #87107

Ecuación de reacción

benzonitrile

DIPEA

tert-butyl ((2S)-4-methyl-3-oxo-1-(2-oxopyrrolidin-3-yl)pent-4-en-2-yl)carbamate

H2O2

→

tert-butyl ((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-(-2-oxopyrrolidin-3-yl) propan-2-yl)carbamate

Rendimiento 45.4%

Disolventes

water

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe resulting mixture was extracted with EtOAc (50 mL×2)
2. 2
   LavadoThe combined extracts were washed with brine
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=2:1)

Procedimiento

To a solution of tert-butyl ((2S)-4-methyl-3-oxo-1-(2-oxopyrrolidin-3-yl)pent-4-en-2-yl)carbamate (200 mg, 0.67 mmol) in methanol (10 mL) at 0° C. was added 30% H2O2 (1.5 g, 1.4 mmol) followed by addition of benzonitrile (520 mg, 5.00 mmol) and DIPEA (0.87 mL, 5.0 mmol). The reaction mixture was stirred for 8 h at ambient temperature and then diluted with water (25 mL). The resulting mixture was extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=2:1) to afford tert-butyl ((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-(-2-oxopyrrolidin-3-yl) propan-2-yl)carbamate (95 mg, 45% yield) as a yellow oil.

Fuente