triisopropoxyborohydride in tetrahydrofuran; isopropyl alcohol T=-23°C;

1: 98 percent / Et3N / diethyl ether / 2 h 2: 92.6 percent / bromine / ethane-1,2-diol 3: 93 percent / potassium t-butoxide / tetrahydrofuran / 18 h 4: 98 percent / 3N HCl / methanol / 1 h 5: 98 percent / KOH / methanol / 0.5 h View Scheme

1: 92.6 percent / bromine / ethane-1,2-diol 2: 93 percent / potassium t-butoxide / tetrahydrofuran / 18 h 3: 98 percent / 3N HCl / methanol / 1 h 4: 98 percent / KOH / methanol / 0.5 h View Scheme

palladium on activated charcoal; hydrogen in ethanol

triethylamine in tetrahydrofuran T=80°C; 8 h;