tert-Butyl Phenyl Carbonate

Typical Procedure (Mono Carbamate Protection of Aliphatic Diamines): tert-Butyl phenyl carbonate (10 mmol) is added to a stirring solution of diamine (5.0 mmol) in absolute EtOH (20 mL). The reaction mixture is refluxed over night followed by removal of the volatiles in vacuo. H2O (25 mL) is added and the pH adjusted to 3 by addition of aq. HCl (2 M) followed by extraction with CH2Cl2 (2 × 50 mL). The aq phase is then made strongly alkaline by addition of aq. NaOH (2 M) and extracted with CH2Cl2 (3 × 80 mL). The organic phase is dried (Na2SO4), filtered and concentrated in vacuo to afford the desired products.