Multi-step reaction with 8 steps
1: 97 percent / conc. H2SO4 / Heating
2: 1.) KH, 2.) 18-crown-6 / 1.) THF, RT, 20 min, 2.) RT
3: 98 percent / H2, / 10percent Pd/C / ethyl acetate / 3 h
4: 99.8 percent / trifluoroacetic acid / CH2Cl2 / 3 h / 0 °C
5: 1.) 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole hydrate / 1.) CHCl3, 0 deg C, 15 min, 2.) RT, 12 h
6: 87 percent / trifluoroacetic acid / tetrahydrofuran / 4 h / Ambient temperature
7: 71 percent / N-methylmorpholine / CH2Cl2 / 3.5 h / Ambient temperature
8: 96 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
With
4-methyl-morpholine; lithium aluminium tetrahydride; 18-crown-6 ether; sulfuric acid; hydrogen; potassium hydride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/ja00175a039