1: 94 percent / diethyl ether / 0.5 h / Ambient temperature 2: 93 percent / PCC/Al2O3, NaOAc / CH2Cl2 / Heating 3: 93 percent / glacial AcOH, NaCNBH3, MgSO4 / methanol / 9 h / Heating 4: 1.) 4N aq. HCl, 2.) H2 / 2.) 10percent Pd/C / 1.) RT, overnight, 2.) 1 atm, 24 h View Scheme

1: 93 percent / PCC/Al2O3, NaOAc / CH2Cl2 / Heating 2: 93 percent / glacial AcOH, NaCNBH3, MgSO4 / methanol / 9 h / Heating 3: 1.) 4N aq. HCl, 2.) H2 / 2.) 10percent Pd/C / 1.) RT, overnight, 2.) 1 atm, 24 h View Scheme

1: 93 percent / glacial AcOH, NaCNBH3, MgSO4 / methanol / 9 h / Heating 2: 1.) 4N aq. HCl, 2.) H2 / 2.) 10percent Pd/C / 1.) RT, overnight, 2.) 1 atm, 24 h View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal 1.) RT, overnight, 2.) 1 atm, 24 h; Yield given. Multistep reaction. Yields of byproduct given;