Multi-step reaction with 7 steps
1: Et3N / 13 °C / 1.) -10 deg C, 20 min, 2.) RT, 30 min
2: diethyl ether / 0.17 h / Ambient temperature
3: 63 percent / silver benzoate, Et3N / 0.5 h / Ambient temperature
4: 93 percent / H2 / 20percent Pd(OH)2/C / methanol / 7 h / 760 Torr / Ambient temperature
5: 54 percent / NaHCO3, MsCl / acetonitrile / 16 h / Heating
6: 95 percent / DIEA / CH2Cl2 / 16 h / Ambient temperature
7: 1.) LDA, 2.) (MeO)3P, O2 / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 3 h
With
hydrogen; oxygen; silver benzoate; sodium hydrogencarbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; phosphorous acid trimethyl ester;
palladium dihydroxide;
In
methanol; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jm980131z