pyridine hydrochloride; lithium diisopropyl amide Multistep reaction;

sodium hydroxide

1: 90 percent / pyridine hydrochloride / methanol; pyridine; various solvent(s) / 36 h / Ambient temperature 2: 1) water 2.) NH4OAc, NaCNBH3 / 1) β-glucosidase / 2.) pH=6.2, 18 h 3: 1.) 3percent HCl, 2.) NaCNBH3 / 1.) aq MeOH, reflux, 40 min 4: 2.) CF3CO3H, Na2HPO4 / 1.) 0 grad C, 2.) CH2Cl2, rt, 12 h 5: 1.) K2CO3 / 1.) MeOH, rt, 2 h, 2.) toluene, EtOH, reflux 24 h View Scheme

ammonia; 1,1'-carbonyldiimidazole in tetrahydrofuran; methanol