Multi-step reaction with 8 steps
1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) 0 deg C, 15 min., THF, 2.) THF, 0 deg C, 1 h
2: 0.479 g / tetrahydrofuran / 0.5 h / 0 °C
3: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature
4: 82 percent / pyridine / 24 h / Ambient temperature
5: 1) 0.1 N aq.NaOH, 2) 0.1 N aq.NaOH / 1) EtOH, reflux, 15 min, 2) EtOH, reflux, 30 min
6: 80 percent / pyridine / 24 h / Ambient temperature
7: 68 percent / LiN3 / dimethylformamide / 4 h / 90 °C
8: 90 percent / Me3SiBr / dimethylformamide / 16 h / Ambient temperature
With
4-methyl-morpholine; pyridine; sodium hydroxide; lithium azide; trimethylsilyl bromide; tetrabutyl ammonium fluoride; isobutyl chloroformate;
In
tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)88721-4