1: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 2: HCO2NH4; Pd/C / methanol / Heating 3: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane 4: TBAF / tetrahydrofuran / 0 °C 5: TEMPO; NaClO2; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C 6: TBTU; DIEA / dimethylformamide / 20 °C View Scheme

1: methylmagnesium bromide With copper(l) iodide in tetrahydrofuran; diethyl ether T=-30°C; 0.166667 h; 2: With boron trifluoride diethyl etherate in tetrahydrofuran; diethyl ether T=-65°C; 0.0833333 h; 3: (R)-N-[(4'-tert-butyldimethylsilyloxymethyl-cyclohexyl)methylidene]-1-phenylethanamine With ammonia; ammonium chloride more than 3 stages;

1: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 2: HCO2NH4; Pd/C / methanol / Heating View Scheme

1: CuI; BF3*Et2O / tetrahydrofuran / -65 - -30 °C 2: HCO2NH4; Pd/C / methanol / Heating 3: aq. NaHCO3; Na2CO3 / 1,2-dimethoxy-ethane View Scheme