HCID 10253545, compound → HCID 10002590, compound

Participants

Reaction Steps

A mixture of tert-butyl 3-[[N-(tert-butoxycarbonyl)-N-phenethylamino]methyl]-4-nitrobenzoate (2.7 g, 5.9 mmole), 10% Pd/C (0.6 g, 0.6 mmole Pd), and EtOAc (60 mL) was shaken under H2 (50 psi). After 3 hr, the mixture was filtered to remove the catalyst, and the filtrate was concentrated to dryness. Flash chromatography on silica gel (20% EtOAc/hexanes) gave the title compound (2.3 g, 91%) as a yellow foamy oil which slowly partially solidified: 1H NMR (250 MHz, CDCl3) δ 7.74 (dd, J=8.4, 2.0 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H), 7.05-7.40 (m, 5H), 6.57 (d, J=8.4 Hz, 1H), 5.00 (br s, 2H), 4.30 (s, 2H), 3.32 (app. t, 2H), 2.69 (app. t, 2H), 1.59 (s, 9H), 1.46 (s, 9H); MS (ES) m/e 449.2 (M+Na)+, 427.2 (M+H)+.

Provenance & Evidence