Multi-step reaction with 13 steps
1: HBTU; DIPEA / tetrahydrofuran / 0.5 h / 20 °C
2: 64 percent / triphenylphosphine; CBr4 / tetrahydrofuran / 0.5 h / 20 °C
3: NaI / acetone / 4 h / Heating
4: K2CO3 / dimethylformamide
5: 55 percent / aq. NaOH / methanol / 1 h / 0 °C
6: N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C
7: tetrahydrofuran; diethyl ether / 0.5 h
8: 90 percent / HBr / ethyl acetate; tetrahydrofuran / -10 °C
9: 51 percent / NaBH4 / ethanol / 0.08 h / -15 °C
10: 93 percent / NaOMe / tetrahydrofuran; methanol / 0.25 h / 20 °C
11: 85 percent / DIPEA / ethanol / Heating
12: 55 percent / DIPEA / tetrahydrofuran; H2O / 0.5 h / 20 °C
13: 81 percent / aq. HCl / methanol / 2 h / Heating
With
4-methyl-morpholine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; carbon tetrabromide; hydrogen bromide; sodium methylate; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm010414i