1: 50 percent / NaN(SiMe3)2 / tetrahydrofuran 2: 1) p-TsOH; 2) 2percent aq. NaOH / 1) MeOH; 2) Et2O 3: 90 percent / iBu2AlH / tetrahydrofuran / -40 °C 4: 1) Ac2O; 2) Li / 1) pyridine; 2) EtNH2, -78 degC View Scheme

1: 50 percent / NaN(SiMe3)2 / tetrahydrofuran 2: 1) p-TsOH; 2) 2percent aq. NaOH / 1) MeOH; 2) Et2O 3: 90 percent / iBu2AlH / tetrahydrofuran / -40 °C View Scheme

1: 50 percent / NaN(SiMe3)2 / tetrahydrofuran 2: 1) p-TsOH; 2) 2percent aq. NaOH / 1) MeOH; 2) Et2O View Scheme