反应详情

A slurry of tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate (500 mg, 1.73 mmol), phenylboronic acid (418 mg, 3.43 mmol), cupric acetate (314 mg, 1.73 mmol), triethyl amine (1.21 mL 1.8 mmol), and 4 Å powdered sieves (300 mg) in dichloromethane (15 mL) was stirred 18 h at ambient temperature. The reaction mixture was diluted with additional solvent and filtered to remove solid material, washed successively with 1N NaOH and brine, and dried over Na2SO4 to provide a brown oil. This material was purified by column chromatography (1:4 ethyl acetate:heptane) to provide the intermediate Boc-protected material (190 mg, 33%). This material was dissolved in dichloromethane (20 mL) and stirred with trifluoroacetic acid (1 mL) for 3 d at ambient temperature. The reaction was concentrated to a foam that was dissolved in toluene and re-evaporated to give the title compound which was used in the next reaction.

1. additionThe reaction mixture was diluted with additional solvent
2. filtrationfiltered
3. customto remove solid material
4. washwashed successively with 1N NaOH and brine
5. dry with materialdried over Na2SO4
6. customto provide a brown oil
7. customThis material was purified by column chromatography (1:4 ethyl acetate:heptane)
8. customto provide the intermediate Boc-protected material (190 mg, 33%)
9. concentrationThe reaction was concentrated to a foam that
10. dissolutionwas dissolved in toluene
11. customre-evaporated