Acetic Acid → 4-isopropyl-N-[4-((S)-1-ethyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide

0.3 g of 4-Isopropyl-N—((S)-4-pyrrolidin-3-yl-phenyl)-benzenesulfonamide (0.87 mmol) were dissolved in 20 ml dichloromethane. After addition of 0.07 ml of acetic acid, 0.073 ml of acetaldehyde (1.31 mmol) and 0.277 g of sodium triacetoxyborohydride (1.31 mmol), the reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated, the residue dissolved in water and the pH adjusted to pH 8-9 with aqueous sodium hydroxide solution. The aqueous phase was extracted three times with diethyl ether, the combined organic phases dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography (chromabond column) with dichloromethane, dichloromethane/methanol 4% as eluent to yield 64 mg of the title compound.

1. customThe solvent was evaporated
2. dissolutionthe residue dissolved in water
3. extractionThe aqueous phase was extracted three times with diethyl ether
4. dry with materialthe combined organic phases dried over magnesium sulfate
5. filtrationfiltered
6. customthe solvent evaporated under reduced pressure
7. customThe crude product was purified via silica gel chromatography (chromabond column) with dichloromethane, dichloromethane/methanol 4% as eluent

ORD-Eintrag

ord-487fef36071c41208366af087cc91c6b

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08470810B2