반응 #170245

반응 방정식

triethylamine

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

→

title compound

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

용매

ethyl acetate

ethanol

반응 조건

후처리

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

실험 절차

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%).

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