1: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 2: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 3: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C View Scheme

4-methyl-morpholine in dichloromethane 1) r.t to 40 deg C 2) 1 h;

1: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 2: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 3: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 4: ethanol / 2 h / Heating 5: KOH / ethanol; H2O / 10 h / Heating View Scheme

1: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 2: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 3: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 4: ethanol / 2 h / Heating View Scheme

1: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 2: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 3: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 4: ethanol / 2 h / Heating 5: KOH / ethanol; H2O / 10 h / Heating 6: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in methanol

N-ethyl-N,N-diisopropylamine in nitromethane 12 h;