Water → N-(3-{3-[3-(3,4-Dichlorophenyl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

To a solution of N-(3-{3-[3-(3,4-dichlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 119, 30 mg, 0.06 mmol) in anhydrous tetrahydrofuran (1 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.12 ml, 0.12 mmol) and the mixture was stirred at room temperature for 3 h. The rapidly stirred reaction mixture was treated sequentially with water (0.12 ml), sodium hydrogen carbonate (200 mg) and ethyl acetate (10 ml). After 30 min the reaction mixture was filtered and concentrated in vacuo to give a colourless oil. This was purified by preparative HPLC (condition 8) to afford the title compound as a pale yellow oil (5.2 mg, 19%).

1. customThe rapidly stirred reaction mixture
2. filtrationAfter 30 min the reaction mixture was filtered
3. concentrationconcentrated in vacuo
4. customto give a colourless oil
5. customThis was purified by preparative HPLC (condition 8)

ORD record

ord-4dba4c9de6eb4740990b06e66e001f65

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2