Benzaldehyde → N-Benzyl-N'-boc-ethylenediamine

To a solution of tert-butyl 2-aminoethylcarbamate (6.4 g, 40.0 mmol) in methanol (60 mL) was added benzaldehyde (4.7 g, 44.0 mmol) and molecular sieve 3 Å. After stirring at ambient temperature overnight, the mixture was cooled down to ca. −10° C. (ice/salt bath) and treated portion wise with NaBH4 (9.1 g, 240.0 mmol) over 30 min. After complete addition, the bath was removed and the reaction mixture stirred at ambient temperature for 16 h. The solvent was evaporated and the residue taken into EtOAc (150 mL) and poured into water (100 mL). The organic layer was extracted with 0.5 N HCl (3×100 mL). The combined aqueous solution was cooled to 0° C., basified with sat. NaHCO3 and extracted with CHCl3 (3×100 mL). The combined organic layers were washed with brine (200 mL). After drying over MgSO4 and filtering, the solvent was evaporated in vacuo to give compound A (9.2 g, 36.8 mmol, 92%) as a colorless oil. LC-MS [M+H] 251.2 (C14H22N2O2+H, calc: 251.3). TLC Rf (DCM/MeOH 9:1): 0.30. Compound A was used without further purification.

1. temperaturethe mixture was cooled down to ca. −10° C. (ice/salt bath)
2. additionAfter complete addition
3. customthe bath was removed
4. stirringthe reaction mixture stirred at ambient temperature for 16 h
5. customThe solvent was evaporated
6. additionpoured into water (100 mL)
7. extractionThe organic layer was extracted with 0.5 N HCl (3×100 mL)
8. temperatureThe combined aqueous solution was cooled to 0° C.
9. extractionextracted with CHCl3 (3×100 mL)
10. washThe combined organic layers were washed with brine (200 mL)
11. dry with materialAfter drying over MgSO4
12. filtrationfiltering
13. customthe solvent was evaporated in vacuo

ORD record

ord-23b3263be61f4c25a11b16c49649fd07

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040032B2