Piperidine → HCID 86759979, compound

Participants

Reaction Steps

A solution of (±)-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester (0.92 g, 1.7 mmol) and piperidine (0.5 mL) in DMF (10 mL) was allowed to stand at rt for 30 min. The reaction mixture was diluted with EtOAc to 100 mL, washed with 10% LiCl solution (2×50 mL) and dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1:1) gave the title compound as colorless oil (0.462 g, 85.5%): 1H NMR (CDCl3) δ 7.26 (m, 2H), 7.20 (m, 1H), 7.10 (d, 2H, J=7.15 Hz), 7.00 (d, 1H, J=4.4 Hz), 6.42 (d, 1H, J=4.4 Hz), 5.43 (d, 1H, J=16.5 Hz), 5.23 (d, 1H, J=16.5 Hz), 3.67 (t, 1H, J=6.62 Hz), 1.83 (m, 1H), 1.57 (m, 1H), 0.83 (t, 3H, J=7.15 Hz); 13C NMR (CDCl3) δ 154.6, 136.3, 129.0, 127.8, 126.3, 117.7, 117.2, 110.0, 108.4, 53.6, 44.4, 29.7, 10.5; MS (ESI+), 316.99, 319.31 (M++H).

Provenance & Evidence