Multi-step reaction with 8 steps
1: 90 percent / TsOH / 18 h / 25 °C
2: diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature
3: 4 N aq, KOH / methanol / 48 h
4: oxalyl chloride, DMF / ethyl acetate / 1 h
5: DMAP / CH2Cl2 / 18 h / Ambient temperature
6: 1.) Me3Al / 1.) THF, toluene, 30 min, 2.) THF, toluene, a) overnight, b) 50 deg C, 24 h
7: triethylamine / CH2Cl2 / 1 h / -10 °C
8: 1.38 g / NaN3 / dimethylformamide / 5 h
With
dmap; potassium hydroxide; sodium azide; oxalyl dichloride; trimethylaluminum; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide;
In
methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm9603633