Multi-step reaction with 7 steps
1: 1.) SOCl2, 2.) aq. NH3 / 1.) methanol, RT, 2 h, 2.) methanol
2: 91 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating
3: 56 percent / H2 / 5percent Pd/C / ethanol / 760 Torr
4: 96 percent / acetonitrile / 0.5 h / Ambient temperature
5: 1.) 1,1'-carbonyldiimidazole, 3.) LiOH
6: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) N-methylmorpholine / 1.) dichloromethane, -68 deg C, 2.5 h, 2.) dichloromethane, -20 deg C, 45 min
7: HCl, NaBH3CN, 3A molecular sieves / methanol / 18 h / Ambient temperature
With
4-methyl-morpholine; hydrogenchloride; lithium hydroxide; ammonium hydroxide; lithium aluminium tetrahydride; thionyl chloride; oxalyl dichloride; 3 A molecular sieve; hydrogen; sodium cyanoborohydride; dimethyl sulfoxide; 1,1'-carbonyldiimidazole;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; acetonitrile;
DOI:10.1021/jm00067a004