Water → N-(3-{6-Methyl-3-[3-(2-thienyl)propyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

To a solution of N-(3-{6-methyl-3-[3-(2-thienyl)propanoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 125, 200 mg, 0.49 mmol) in anhydrous tetrahydrofuran (7.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.99 ml, 0.99 mmol) and the mixture was stirred at room temperature for 2 h. The rapidly stirred reaction mixture was treated sequentially with water (1.0 ml), sodium hydrogen carbonate (1.0 g) and ethyl acetate (25 ml). After 15 min the reaction mixture was filtered and concentrated in vacuo to afford a light yellow oil. This was purified by chromatography using a Biotage Flash 12™ cartridge packed with silica gel (8 g) eluting with hexane: ethyl acetate (100:0 to 0:100) to afford the title compound as a colourless oil (135 mg, 70%).

1. customThe rapidly stirred reaction mixture
2. filtrationAfter 15 min the reaction mixture was filtered
3. concentrationconcentrated in vacuo
4. customto afford a light yellow oil
5. customThis was purified by chromatography
6. washeluting with hexane: ethyl acetate (100:0 to 0:100)

ORD-Eintrag

ord-da1b21ea094441fd936843fc4237d002

Quelldatensatz

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07049444B2