1,1'-Carbonyldiimidazole → HCID 86629525, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methoxylamine hydrochloride (0.520 g, 6.25 mmol) in CH3CN (15 ml) was added DIPEA (1.09 ml, 6.25 mmol) followed by CDI (1.02 g, 6.25 mmol) and the reaction stirred at rt for 1.5 h after which a solution of the amine from above (0.880 g, 3.12 mmol) in CH3CN (10 ml) was added and the reaction stirred at 60° C. overnight. The solution was cooled, treated with saturated aqueous NaHCO3 (20 ml) and extracted with CH2Cl2 (3×15 ml). The combined organic extracts were dried (Na2SO4), filtered, and concentrated. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v) gave 4-(3-methoxy-1-thiophen-3-ylmethyl-ureido)-piperidine-1-carboxylic acid tert-butyl ester as a white foam (0.95 g, 86%). 1H-NMR (CDCl3) δ 1.43 (s, 9H), 1.54 (m, 1H), 1.75 (d, 2H, J=9.0 Hz), 2.79 (br t, 1H), 3.65 (s, 3H), 4.17 (m, 2H), 4.27 (s, 2H), 6.96 (d, 1H, J=3.0 Hz), 7.08 (s, 1H), 7.11 (s, 1H), 7.36 (m, 1H).

Provenance & Evidence