Réaction #73530

Équation de réaction

6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-[3-(benzyloxy)propyl]-N-cyclopentylpyridine-3-sulfonamide

boron tribromide

MeOH

→

6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-cyclopentyl-N-(3-hydroxypropyl)pyridine-3-sulfonamide

Rendement 86.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   Lavagewashed successively with saturated NaHCO3 solution (30 mL) and brine (30 mL)
2. 2
   Séchagedried over Na2SO4
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   Autrepurified by chromatography on a column of silica gel
5. 5
   Lavageeluting with a 9/1 DCM/MeOH mixture

Mode opératoire

To a solution of 150 mg (0.27 mmol) of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-[3-(benzyloxy)propyl]-N-cyclopentylpyridine-3-sulfonamide in 2 mL of DCM is added dropwise, at −78° C. under argon, 0.82 mL (0.82 mmol) of boron tribromide (1M in DCM). Stirring is continued for 1 hour at −78° C., and 2 mL of MeOH are then added at 0° C. The medium is taken up in 40 mL of DCM, washed successively with saturated NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a 9/1 DCM/MeOH mixture. 106 mg of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-cyclopentyl-N-(3-hydroxypropyl)pyridine-3-sulfonamide are thus obtained in the form of a powder.

Source