Reaction #170245

Reaction equation

triethylamine

1-benzhydryl-3-(benzofuran-2-yl)-3-chloroazetidine

→

title compound

1-Benzhydryl-3-(benzofuran-2-yl)azetidine

Solvents

ethyl acetate

ethanol

Conditions

Workup

1. 1
   workup.WAITwas continued under same conditions for 3 days
2. 2
   OtherAfter removal of hydrogen
3. 3
   workup.ADDITIONthe mixture was diluted with dichloromethane (50 mL)
4. 4
   Filtrationfiltered through Clarcel®
5. 5
   Concentrationconcentrated
6. 6
   Washwashed with aqueous saturated sodium hydrogencarbonate (30 mL)
7. 7
   WashThe aqueous layer was back-washed with dichloromethane (2×30 mL) and all the combined organic layers
8. 8
   Dryingwere dried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated
11. 11
    OtherThe residue was purified by chromatography on silica gel

Procedure

A mixture of 1-benzhydryl-3-(benzofuran-2-yl)-3-chloroazetidine (458 mg, 1.23 mmol) and 10% palladium on carbon (130 mg) in ethyl acetate (6 mL) and ethanol (6 mL) was stirred at room temperature under hydrogen atmosphere (˜1 atm) for 1 day. An additional amount of 10% palladium on carbon (130 mg) was added as well as triethylamine (171 μL, 1.23 mmol) and hydrogenation was continued under same conditions for 3 days. After removal of hydrogen, the mixture was diluted with dichloromethane (50 mL), filtered through Clarcel® and concentrated. The residue was taken up in dichloromethane (30 mL) and washed with aqueous saturated sodium hydrogencarbonate (30 mL). The aqueous layer was back-washed with dichloromethane (2×30 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. The title compound was obtained as a yellow gum (111 mg, 27%).

Source