Benzyl Alcohol → HCID 69464031, compound

Participants

Reaction Steps

To a suspension of 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-oxo-butyric acid tert-butyl ester (1.24 g, 3.14 mmol) in Dichloromethane (10 mL) at room temperature was added 0.20 equiv TsOH.H2O (0.12 g, 0.63 mmol) and followed by dropwise 5.0 equiv of Benzyl alcohol (1.62 mL, 15.68 mmol). After stirring room temperature for 18 hrs, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to obtain a crude title compound. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (10–40%) to give the title compound (0.75 g, 40%) as clear oil. TLC (40% EtOAc/Hexane) Rf=0.68; 1HNMR (CDCl3) δ 7.76 (d, J=7.2 Hz, 2H), 7.59 (d, J=7.5 Hz, 2H), 7.39 (t, J=7.5 Hz, 21H), 7.35–7.27 (m, 12H), 5.37 (d, J=9.6 Hz, 1H), 4.73–4.52 (m, 5H), 4.35 (d, J=6.6 Hz, 2H), 4.24–4.16 (q, J=6.6 Hz, 2H), 2.55–2.50 (m, 2H), 1.39 (s, 9H). MS(ES) for C37H39NO9 (MW=593.71): positive 611 (M+NH4+).

Provenance & Evidence