HCID 68431882, compound → HCID 86074989, compound

Participants

Reaction Steps

The lower Rf isomer of ethyl 5-benzyloxycarbonyl-2-(4-fluorobenzyl)-3-oxo-2,5-diazabicyclo[4.1.0]heptane-7-carboxylate (7.5 g, 17.5 mmol) and 10% palladium on carbon (940 mg; 0.05 mmol) in ethanol (200 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature overnight. The product mixture was filtered through a pad of Celite, and concentrated under vacuum to provide the title compound. The structure was assigned by the analysis of HMQC, gHMBC and ROESY spectra. 1H NMR (400 MHz, CDCl3) δ 7.24 (dd, J=8.4, 5.3 Hz, 2H), 7.01 (t, J=8.6 Hz, 2H), 5.22 (d, J=15.0 Hz, 1H), 4.13 (q, J=7.2 Hz, 2H), 3.95 (d, J=14.8 Hz, 1H), 3.64-3.80 (m, 1H), 3.61 (d, J=4.5 Hz, 2H), 2.95-3.06 (m, 2H), 2.84 (dd, J=16.1, 9.4 Hz, 1H), 2.59 (dd, J=16.1, 2.4 Hz, 1H), 1.26 (t, J=7.2 Hz, 3H). ES MS (M+1)=295.32.

Provenance & Evidence