3-[Benzyl-(1(R)-phenylethyl)-amino]-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester → 3-Amino-3-(2-fluoro-biphenyl-4-yl)-propionic acid ethyl ester

Participants

Reaction Steps

A solution of the dibenzylamine 13-3 (5.65 gm, 11.75 mmol) in EtOH/HOAc (90/10 mL) was purged with argon and treated with Pd(OH)2 (3 g) and placed under 1 atm of H2 gas for 12 h. Additional portions (2.5 g) or Pd(OH)2 were added after 24 h, 48 h and 144 h. The reaction mixture was purged with argon, filtered through Celite, and the filtrate dissolved in aq HCl (pH=1) The aqueous solution was washed with EtOAc, neutralized with satd aq NaHCO3, and extracted with EtOAc (3×30 mL). The combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated to give the desired product 13-4.

Provenance & Evidence