Multi-step reaction with 8 steps
1: 94 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
2: 93 percent / 2M aq. NaOH / methanol / 0.5 h / Ambient temperature
3: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) THF, DMF, RT, 3 h
4: 82 percent / a) borane-dimethyl sulfide complex, b) 10percent aq. HCl / a) THF, 70 deg C, 1 h, b) THF, MeOH, 70 deg C, 1 h
5: DMSO, oxalyl chloride / CH2Cl2 / a) -20 deg C,
6: 30 percent / tetrahydrofuran / 1 h / -78 °C
7: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) THF, DMF, RT, 3 h
8: 1.) borane-THF complex, 2.) 3N aq. NaOH, 30percent H2O2 / 1.) THF, 40 deg C, 45 min, 2.) THF, 60 deg C, 30 min
With
hydrogenchloride; sodium hydroxide; borane-THF; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1248/cpb.41.1717