Reaction #170242

Reaction equation

triethylamine

1-benzhydryl-3-(benzofuran-3-yl)-3-chloroazetidine

→

title compound

1-Benzhydryl-3-(benzofuran-3-yl)azetidine

Solvents

ethyl acetate

ethanol

Conditions

Workup

1. 1
   OtherAfter removal of hydrogen
2. 2
   workup.ADDITIONthe mixture was diluted with dichloromethane (100 mL)
3. 3
   Filtrationfiltered through Clarcel®
4. 4
   Concentrationconcentrated
5. 5
   Washwashed with aqueous saturated sodium hydrogencarbonate (50 mL)
6. 6
   WashThe aqueous layer was back-washed with dichloromethane (2×50 mL) and all the combined organic layers
7. 7
   Dryingwere dried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated
10. 10
    OtherThe residue was purified by chromatography on silica gel

Procedure

A mixture of 1-benzhydryl-3-(benzofuran-3-yl)-3-chloroazetidine as obtained in the previous step (873 mg, ≦2.14 mmol), triethylamine (299 μL, 2.14 mmol) and 10% palladium on carbon (227 mg) in ethyl acetate (15 mL) and ethanol (15 mL) was stirred at room temperature under hydrogen atmosphere (˜1 atm) for 3 days. After removal of hydrogen, the mixture was diluted with dichloromethane (100 mL), filtered through Clarcel® and concentrated. The residue was taken up in dichloromethane (50 mL) and washed with aqueous saturated sodium hydrogencarbonate (50 mL). The aqueous layer was back-washed with dichloromethane (2×50 mL) and all the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (100:0 to 95:5) as eluent followed by preparative TLC on reversed phase C18 using acetonitrile/water (90:10) as eluent. The title compound was obtained as a yellow gum (52 mg, 7%).

Source