hydrogenchloride in tetrahydrofuran; methanol 24 h; Ambient temperature;

1: 1.) LDA, 2.) hexamethylphosphoric triamide (HMPT) / 1.) THF, hexane, from -30 deg C to RT, 30 min, 2.) THF, hexane, reflux, 16 h 2: 1N aq. HCl / tetrahydrofuran; methanol / 24 h / Ambient temperature View Scheme

1: 1.) LDA, 2.) hexamethylphosphoric triamide (HMPT) / 1.) THF, hexane, from -30 deg C to RT, 30 min, 2.) THF, hexane, reflux, 16 h 2: 1N aq. HCl / tetrahydrofuran; methanol / 24 h / Ambient temperature View Scheme

pyridine; hydrogen; palladium on barium sulfate

1: H2, Py / Pd-BaSO4 2: NaBH4 / ethanol View Scheme