Tert-butyl N-[2-(benzylaMino)ethyl]carbaMate

57260-73-8

100-52-7

174799-52-1

The general procedure for the synthesis of tert-butyl (2-(benzylamino)ethyl)carbamate from N-tert-butoxycarbonyl-1,2-ethylenediamine and benzaldehyde is as follows: 1. benzaldehyde (4.7 g, 44.0 mmol) was added to a methanol (60 mL) solution of N-Boc-1,2-ethylenediamine (6.4 g, 40.0 mmol). 2. The reaction mixture was stirred at room temperature overnight. 3. The reaction mixture was cooled to -10 °C (using an ice/salt bath) and NaBH4 (9.1 g, 240.0 mmol) was added in batches over 30 minutes. 4. After the addition was complete, the ice bath was removed and the reaction mixture was continued to be stirred at room temperature for 16 hours. 5. The solvent was evaporated and the residue was dissolved in EtOAc (150 mL) and poured into water (100 mL). 6. The organic layer was extracted with 0.5N HCl (3 x 100 mL). 7. The combined aqueous phases were cooled to 0°C and alkalized with saturated NaHCO3 solution. 8. The alkalized aqueous phase was extracted with CHCl3 (3 x 100 mL). 9. Combine the organic layers and wash with brine (200 mL). 10. Dry the organic layer with MgSO4, filter and evaporate the solvent in vacuum to obtain the target product tert-butyl (2-(benzylamino)ethyl)carbamate (9.2 g, 36.8 mmol, 92% yield) as a colorless oil. Product Characterization: - LC-MS [M + H]+: 251.2 (C14H22N2O2 + H, calculated value: 251.3). - TLC Rf (DCM/MeOH 9:1): 0.30.