Benzyl Bromide → HCID 10891827, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-ethyl 2-aminopropanoate hydrochloride (4.59 g, 30.0 mmol) and K2CO3 (12.4 g, 90.0 mmol) in MeCN was added (bromomethyl)benzene (12.9 g, 75.0 mmol) at RT. The mixture was stirred at 70° C. for 14 h. The reaction mixture was quenched with aq. NH4Cl. After concentration, the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (100:1) to afford 8.8 g (98%) of (S)-ethyl 2-(dibenzylamino)propanoate (26): LCMS (ESI) m/z: 298.2 [M+11]+.

Provenance & Evidence