ammonia; sodium in tetrahydrofuran

1: 87 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 3: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 4: 45 percent / LiBH4 / tetrahydrofuran 5: 69 percent / pyridine 6: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 87 percent / Et3N / dioxane; H2O / 15 h / 50 °C 2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 3: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 4: 45 percent / LiBH4 / tetrahydrofuran 5: 69 percent / pyridine 6: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 77 percent / HCl (gas) / 5 h / Heating 2: 87 percent / Et3N / dioxane; H2O / 15 h / 50 °C 3: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 4: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 5: 45 percent / LiBH4 / tetrahydrofuran 6: 69 percent / pyridine 7: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 2: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 3: 45 percent / LiBH4 / tetrahydrofuran 4: 69 percent / pyridine 5: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 2: 45 percent / LiBH4 / tetrahydrofuran 3: 69 percent / pyridine 4: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 57 percent / HCl / Heating 2: 81 percent / Et3N / H2O; dioxane 3: 45 percent / LiBH4 / tetrahydrofuran 4: 69 percent / pyridine 5: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 69 percent / pyridine 2: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 45 percent / LiBH4 / tetrahydrofuran 2: 69 percent / pyridine 3: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

1: 81 percent / Et3N / H2O; dioxane 2: 45 percent / LiBH4 / tetrahydrofuran 3: 69 percent / pyridine 4: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme