Multi-step reaction with 17 steps
1: amberlyst 15 / 2 h / 0 °C
2: benzene; diethyl ether / 0.58 h
3: pyridinium p-toluenesulfonate / acetone / 0.33 h / Ambient temperature
4: 84 percent / N-ethyldiisopropylamine / CH2Cl2 / 46 h / Ambient temperature
5: sodium hydride / tetrahydrofuran / 6.5 h / Ambient temperature
6: triethylamine / 1.) 0 deg C, 1h; 2.) rt, 36h
7: potassium hydroxide / methanol; H2O / 2.5 h / Heating
8: 87 percent / hydroxylamine hydrochloride, sodium acetate / methanol / 0.67 h / Heating
9: xylene / 0.83 h / 150 °C
10: sodium hydroxide / ethanol; H2O / 7.25 h / Heating
11: 84 percent / H2, (1S)-(+)-10-camphorsulfonic acid / palladium hydroxide on carbon / ethyl acetate / 22.5 h
12: 85 percent / N-ethyldiisopropylamine / 4-dimethylaminopyridine / CH2Cl2 / 1.) 0 deg C, 40 min; 2.) rt,1.33 h
13: lithium diisopropylamide / hexane; tetrahydrofuran / 1.) 0 deg C, 50 min; 2.) rt, 50 min
14: 83 percent / n-BuLi / hexane; tetrahydrofuran / 1.1 h / Ambient temperature
15: 71 percent / dicyclohexylcarbodiimide, pyridine, trifluoroacetic acid, DMSO / benzene / 4.5 h / Ambient temperature
16: 69 percent / camphorsulfonic acid / 2.5 h / Ambient temperature
17: 83 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / Ambient temperature
With
pyridine; potassium hydroxide; sodium hydroxide; n-butyllithium; Amberlyst 15; tributylphosphine; camphor-10-sulfonic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide;
dmap; palladium dihydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; acetone; xylene; benzene;
DOI:10.1016/S0040-4020(01)83440-2