phenylalaninol, (S)- → (S)-2-benzylamino-3-phenyl-1-propanol

Participants

Reaction Steps

To a solution of L-phenylalaninol 3c (where W=H, W=OH, R1=H, R2=Bn, R3=H) (5 g) in MeOH (150 ml) benzaldehyde (3.3 ml) were added. The reaction mixture was stirred at r.t. for 1 h, then 1.2 g of NaBH4, were added in small portions in 2 hr at 0° C. The solvent was evaporated and the residue extracted with 50 ml of HCl at pH=2. The aqueous solution was extracted with Et2O, treated with Na2CO3 until pH=9 and then extracted with CHCl3. The organic phase evaporated gave N-benzyl-(L)-phenylalaninol as white solid (7 g) 3c (where W=H, W=OH, R1=H, R2=Bn, R3=Bn)

Provenance & Evidence