Ethanol → HCID 131734234, compound

Participants

Reaction Steps

To a stirring solution of (1S,2S,4S)-1-acetamido-N-(tert-butyl)-4-(nitromethyl)-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl)cyclopentanecarboxamide (0.907 g, 2.0 mmol) in a mixture of tetrahydrofuran (20 mL), ethyl acetate (15 mL), and ethanol (5 mL) under nitrogen was added Raney nickel (1.2 g). The reaction mixture was then purged with hydrogen and stirred under an atmosphere of hydrogen at room temperature for 6 h. At the end of this period, the mixture was purged with nitrogen, then carefully through Celite®. After rinsing the filter cake with ethyl acetate the combined filtrate was concentrated in vacuo to afford the subject compound (0.841 g, 99%) as a white solid. NMR (CDCl3): δ 6.98 (br s, 1 H), 6.93 (br s, 1 H), 2.55-2.70 (m, 3 H), 2.44 (m, 1 H), 2.24 (m, 1 H), 1.91 (m, 3 H), 1.50-1.65 (m, 3 H), 1.20-1.45 (m, 4 H), 1.26 (s, 9 H), 1.66 (s, 12 H), 0.60-0.75 (m, 2 H). MS (M+1): 424.4.

Provenance & Evidence