Reacción #2358497

Ecuación de reacción

water

(3E,3aR,6aR)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylene]-1,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2-one

NMO

acetone

→

desired compound

Rendimiento 38.0%

(3E,3aR,6aS)-5,6-dihydroxy-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylene]-1,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-one

Rendimiento 38.0%

Disolventes

tBuOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONH2Cl2 was added
2. 2
   Secadothe crude mixture was dried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroPurification

Procedimiento

To a solution of (3E,3aR,6aR)-3-[[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylene]-1,3a,4,6a-tetrahydrocyclopenta[b]pyrrol-2-one Ia-1′ (137 mg, 0.55 mmol) in tBuOH (3 mL) was added NMO (77.9 mg, 0.67 mmol) and acetone (0.5 mL) followed by OsO4 (2.5-wt % in tBuOH, 560 mg, 0.055 mmol) and water (15 mg, 0.84 mmol). After 1 h at room temperature, H2Cl2 was added then the crude mixture was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification using flash chromatography (CH2Cl2/MeOH, gradient) afforded the desired compound as a yellow foam (59 mg, 38%); 1H NMR (400 MHz, MeOH-d4) 7.25 (1H, d), 7.14 (1H, m), 6.34 (1H, m), 4.02 (1H, m), 3.84 (1H, dd), 3.76 (1H, dd), 3.55 (1H, m), 2.15 (1H, dt), 1.96 (3H, dd), 1.86 (1H, ddd): LCMS (Method D): 0.24 min; ES+282 (M+H+).

Fuente