Piperidine → Ethyl acetate methanol ammonium hydroxide

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A solution of N-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-prolinamide (5.06 g, 9.59 mmol) and piperidine (82 mg, 9.59 mmol, 1 equiv) in DMF (20 mL) was stirred for 3 h at room temperature then concentrated in vacuo. Silica gel chromatography (EtOAc to 8:1:1 EtOAc/MeOH/NH4OH) afforded a sticky, yellow, solid which was dissolved in EtOAc and treated with gaseous HCl for 1 h at 0° C. Solvent was removed in vacuo, and the remaining residue was suspended in ether with vigorous stirring. The resulting precipitate was filtered and washed with ether to afford the title compound as an off-white, hygroscopic powder. 1H NMR (400 MHz, CD3OD): δ 9.79 (s, 1 H), 8.95 (s, 1 H), 7.70 (d, J=1.6 Hz, 1 H), 7.61–7.60 (m, 2 H), 4.44–4.41 (m, 2 H), 4.30 (apparent t, J=7.6 Hz, 1 H), 3.39–3.31 (m, 2 H), 2.46–2.40 (m, 1 H), 2.18–1.92 (m, 3 H). LCMS (M+H): 306.0.

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