Acetic Acid → HCID 68685658, compound

Participants

Reaction Steps

To a stirred solution of [benzhydryl-(2-chlorobutyl)amino]acetic acid tert-butyl ester (7.7 g, 19.9 mmol, 1 eq.) in dry THF (120 mL) at −78° C. was added NaHMDS (49.7 mL, 49.6 mmol, 2.5 eq.) dropwise over 45 min. The reaction was then neutralized with AcOH (0.2 mL). The solid formed was filtered off and washed with EtOAc and the filtrate was concentrated in vacuo. The residue was redissolved in EtOAc, washed with brine, dried over MgSO4, filtered, concentrated in vacuo. The resulting product was chromatographed on silica gel using 50% DCM/hexanes/0.5% EtOAc mixture as eluent to afford (+)-trans-1-benzhydryl-3-ethylazetidine-2-carboxylic acid tert-butyl ester 86% yield. ESMS: m/z 352.3 [M+H].

Provenance & Evidence