Multi-step reaction with 15 steps
1: Et3N / diethyl ether / 0.17 h / 0 °C
2: m-chloroperoxybenzoic acid, aq. NaHCO3 / CH2Cl2 / 0.33 h / 0 °C
3: 3N aq. HCl / tetrahydrofuran / 0.25 h / 23 °C
4: H5IO6 / tetrahydrofuran / 1.5 h / 23 °C
5: Et3N / tetrahydrofuran / 2 h / 23 °C
6: 4-dimethylaminopyridine / tetrahydrofuran / 1 h / 23 °C
7: 99 percent / CrO3, aq. H2SO4 / acetone / 0.17 h / 0 °C
8: (COCl)2 / CH2Cl2 / 1 h / 23 °C
9: Et3N / CH2Cl2 / 0.33 h / 23 °C
10: 87 percent / PhOH / diethyl ether / 0.33 h / -78 °C
11: Et3SiH / 10percent Pd/C / acetone / 1 h / 23 °C
12: 1,4-diazabicyclo<2.2.2>octane / CH2Cl2 / 2 h / 23 °C
13: 92 percent / (2S)-1-methyl-2-(1-piperidino)pyrrole, Sn(OTf)2, n-Bu2Sn(OAc) / CH2Cl2 / 18 h / -78 °C
14: 91 percent / i-Pr2-NEt / CH2Cl2 / 5 h / Heating
15: 99 percent / Et3SiH / 10percent Pd/C / acetone / 1 h / 23 °C
With
1,4-diaza-bicyclo[2.2.2]octane; chromium(VI) oxide; hydrogenchloride; triethylsilane; dmap; tin(II) trifluoromethanesulfonate; oxalyl dichloride; 1-methyl-2-(1-piperidino)pyrrole; n-Bu2Sn(OAc); sulfuric acid; sodium hydrogencarbonate; periodic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; phenol;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1021/ja00071a066