Water → HCID 22141355, compound

To a solution of N-(3-{3-[2-(5-chloro-3-thienyl)acetyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 121, 45 mg, 0.11 mmol) in anhydrous tetrahydrofuran (1 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.22 ml, 0.22 mmol) and the mixture was stirred at room temperature for 3 h. The rapidly stirred reaction mixture was treated sequentially with water (0.22 ml), sodium hydrogen carbonate (200 mg) and ethyl acetate (10 ml). After 30 min the reaction mixture was filtered and concentrated in vacuo to afford a pale yellow oil. This was purified by preparative HPLC (condition 8) to give a very pale yellow oil which was partitioned between dichloromethane (10 ml) and aqueous potassium carbonate solution (4% w:v, 5 ml). The layers were separated and the organic layer was washed with water (3 ml), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (14 mg, 33%).

1. customThe rapidly stirred reaction mixture
2. filtrationAfter 30 min the reaction mixture was filtered
3. concentrationconcentrated in vacuo
4. customto afford a pale yellow oil
5. customThis was purified by preparative HPLC (condition 8)
6. customto give a very pale yellow oil which
7. customwas partitioned between dichloromethane (10 ml) and aqueous potassium carbonate solution (4% w:v, 5 ml)
8. customThe layers were separated
9. washthe organic layer was washed with water (3 ml)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-9fbd56de46c44792be33846bc23b163b

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1