Multi-step reaction with 10 steps
1: 96 percent / K2CO3 / dimethylformamide; acetonitrile / Heating
2: 100 percent / 5 N aq. HCl / ethyl acetate / 3 h / Ambient temperature
3: 70 percent / Na(OAc)3BH, Et3N, DCE / Ambient temperature
4: NaHCO3 / tetrahydrofuran; H2O / 1.5 h / Ambient temperature
5: LiN(TMS)2 / tetrahydrofuran / 0 - 20 °C
6: 96 percent / HCl / ethanol / 0 - 20 °C
7: 69 percent / Na(OAc)3BH, Et3N / Ambient temperature
8: 1.) NaHCO3, 2.) aq. LiOH, 3.) Dowex H+
9: 71 percent / EDC, HOBt, DIPEA / acetonitrile / 18 h / Ambient temperature
10: 100 percent / H2 / Pd/C / ethanol; ethyl acetate; H2O / 2585.7 Torr
With
hydrogenchloride; lithium hydroxide; DCE; Dowex H+; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(98)00636-2