Multi-step reaction with 11 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene
2.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 16 h / 20 °C
3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
3.2: 16 h / 80 °C / Sealed tube
4.1: carbon dioxide / methanol / 35 °C / 75007.5 Torr
5.1: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere
6.1: formic acid / diethyl ether / 16 h / 20 °C
7.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -10 °C
7.2: 1.5 h / -10 °C / Molecular sieve
8.1: sodium methylate / methanol; tetrahydrofuran / 0.25 h / -10 °C
9.1: tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate / ethyl acetate / 2.5 h / 20 °C
10.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 14 h / 20 °C / Inert atmosphere
11.1: sodium methylate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C
With
pyridine; formic acid; Hoveyda-Grubbs catalyst second generation; copper(ll) sulfate pentahydrate; trifluoromethylsulfonic anhydride; carbon dioxide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium L-ascorbate; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;