hydrogenchloride in methanol; water 24 h; Heating;

hydrogenchloride in methanol 0.5 h; Heating;

1: 96 percent / Bu3SnH / AIBN / methanol; toluene / 1 h / Heating 2: 94 percent / sodium / methanol / 0.5 h / Ambient temperature 3: 82 percent / 6M-HCl / methanol; H2O / 24 h / Heating View Scheme

1: 93 percent / DEAD, PPh3 / tetrahydrofuran / 0 deg C, RT, 15 min 2: NBS, propylene oxide / CHCl3 / 1 h / Ambient temperature 3: 85 percent / hydrochloric acid / methanol; H2O / 0.5 h / Ambient temperature 4: 96 percent / Bu3SnH / AIBN / methanol; toluene / 1 h / Heating 5: 94 percent / sodium / methanol / 0.5 h / Ambient temperature 6: 82 percent / 6M-HCl / methanol; H2O / 24 h / Heating View Scheme

1: NBS, propylene oxide / CHCl3 / 1 h / Ambient temperature 2: 85 percent / hydrochloric acid / methanol; H2O / 0.5 h / Ambient temperature 3: 96 percent / Bu3SnH / AIBN / methanol; toluene / 1 h / Heating 4: 94 percent / sodium / methanol / 0.5 h / Ambient temperature 5: 82 percent / 6M-HCl / methanol; H2O / 24 h / Heating View Scheme

1: 85 percent / hydrochloric acid / methanol; H2O / 0.5 h / Ambient temperature 2: 96 percent / Bu3SnH / AIBN / methanol; toluene / 1 h / Heating 3: 94 percent / sodium / methanol / 0.5 h / Ambient temperature 4: 82 percent / 6M-HCl / methanol; H2O / 24 h / Heating View Scheme

1: 99 percent / sodium borohydride / propan-2-ol; H2O / 1 h / 0 deg C -> room temperature 2: 87 percent / NBS / CHCl3 / 1 h / Ambient temperature 3: 60 percent / tributyltin hydride, AIBN / toluene; methanol / 1 h / Heating 4: 73 percent / 6 M HCl / methanol / 0.5 h / Heating View Scheme

1: 87 percent / NBS / CHCl3 / 1 h / Ambient temperature 2: 60 percent / tributyltin hydride, AIBN / toluene; methanol / 1 h / Heating 3: 73 percent / 6 M HCl / methanol / 0.5 h / Heating View Scheme

1: 57 percent / diethyl azodicarboxylate, PPh3 / tetrahydrofuran / 0.25 h / Ambient temperature; reactions of cyclohex-2-enol with diacylamines under Mitsunobu reaction conditions, stereocontrolled preparation of cyclohexane amino alcohols 2: 99 percent / sodium borohydride / propan-2-ol; H2O / 1 h / 0 deg C -> room temperature 3: 87 percent / NBS / CHCl3 / 1 h / Ambient temperature 4: 60 percent / tributyltin hydride, AIBN / toluene; methanol / 1 h / Heating 5: 73 percent / 6 M HCl / methanol / 0.5 h / Heating View Scheme

hydrogenchloride Yield given;