lithium aluminium tetrahydride in tetrahydrofuran T=60 - 65°C; 72 h;

1: 1.) 10percent Pd/C / 1.) cyclohexene, MeOH, reflux, 5 h, 2.) MeOH, from 62 to 65 deg C, 110 h 2: 86 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C 3: 74 percent / Na2CO3 / diethyl ether; H2O; toluene / 1 h / 0 °C 4: 79 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C View Scheme

1: 1.) 4-methylmorpholine, ethylchloroformate, 2.) 4-methylmorpholine / 1.) EtOAc, -15 deg C, 15 min, 2.) a.) -15 deg C, 1 h, b.) RT, 12 h 2: 1.) 10percent Pd/C / 1.) cyclohexene, MeOH, reflux, 5 h, 2.) MeOH, from 62 to 65 deg C, 110 h 3: 86 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C 4: 74 percent / Na2CO3 / diethyl ether; H2O; toluene / 1 h / 0 °C 5: 79 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C View Scheme

1: 74 percent / Na2CO3 / diethyl ether; H2O; toluene / 1 h / 0 °C 2: 79 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C View Scheme

1: 86 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C 2: 74 percent / Na2CO3 / diethyl ether; H2O; toluene / 1 h / 0 °C 3: 79 percent / LAH / tetrahydrofuran / 72 h / 60 - 65 °C View Scheme