Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DMF, a) 0 deg C, 10 min, b) 25 deg C, 30 min, 2.) DMF, 75 deg C, 1 h
2: p-TsOH*H2O / methanol / 0.5 h / 45 °C
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 30 min, 2.) CH2Cl2, 0 deg C, 5 min
4: 1.) NaH / 1.) THF, a) 0 deg C, 10 min, b) 25 deg C, 30 min, 2.) THF, 25 deg C, 1 h
5: 99 percent / NaBH4 / methanol / 0.25 h / 0 °C
6: 98 percent / aq. NaOH / methanol; tetrahydrofuran / 16 h / 25 °C
With
sodium hydroxide; sodium tetrahydroborate; oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol;
DOI:10.1016/S0968-0896(97)00090-4