Multi-step reaction with 10 steps
1.1: 91 percent / 3 Angstroem molecular sieves; BF3*OEt2 / CH2Cl2 / 2 h
2.1: 3 Angstroem molecular sieves / CH2Cl2 / 1 h
2.2: 92 percent / NIS; AgOTf / CH2Cl2 / 0.25 h
3.1: 81 percent / NaOMe; MeOH / CH2Cl2 / 12 h / 20 °C
4.1: 86 percent / NIS; TfOH / CH2Cl2 / 2 h / -20 °C
5.1: aq. NH2NH2 / ethanol / 24 h / Heating
6.1: TBAF / tetrahydrofuran / 24 h
7.1: 0.510 g / TBTU; HOBt; N-ethylmorpholine / dimethylformamide / 2 h
8.1: TEMPO; KBr; aq. NaHCO3 / NaOCl / acetonitrile / 1 h / pH 10.5
9.1: piperidine / dimethylformamide / 0.5 h
10.1: 0.22 g / PyBOP / dimethylformamide / 1 h
With
piperidine; N-ethylmorpholine;; methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium methylate; sodium hydrogencarbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; potassium bromide;
sodium hypochlorite;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b416106h