Multi-step reaction with 13 steps
1: 1.) N-methylmorpholine / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, from 10 deg C to RT, 3 h
2: 60 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Heating
3: 96 percent / Et3N, (Ph3)2PPdCl2, CuI / acetonitrile / 4 h / Ambient temperature
4: H2, AcOH / 5percent Pd/C / methanol / 16 h / 2585.7 Torr
5: N-methylmorpholine / CH2Cl2 / 16 h / Ambient temperature
6: 0.75 g / triphenoxymethylphosphonium iodide / acetonitrile / 3 h / Ambient temperature
7: 0.58 g / NaN3 / dimethylformamide / 3 h / 70 °C
8: triphenylphosphine, H2O / tetrahydrofuran / 3 h / 20 - 60 °C
9: CH2Cl2 / 1.5 h / Ambient temperature
10: 0.4 g / 1 M LiOH / tetrahydrofuran / 1.5 h / Ambient temperature
11: 0.3 g / BH3 / tetrahydrofuran / 2 h / -5 - 10 °C
12: 47 percent / imidazole, N-methylmorpholine / acetonitrile / 2.5 h / 60 °C
13: H2 / 10percent Pd/C / ethanol / 1.5 h / 1551.4 Torr
With
4-methyl-morpholine; 1H-imidazole; lithium hydroxide; copper(l) iodide; sodium azide; (Ph3)2PPdCl2; borane; tetrabutyl ammonium fluoride; methyltriphenoxyphosphonium iodide; water; hydrogen; acetic acid; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm980001q