Cesium carbonate → HCID 59349571, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (16.29 g, 50 mmoles, 2 equivalents) was added to a stirred solution of 3-methyl-4-nitrophenol (3.82 g, 25 mmoles, 1 equivalent) and tert-butyl 4-(tosyloxymethyl)piperidine-1-carboxylate (10.16 g, 27.5 mmoles, 1.1 equivalent) in anhydrous DMA (25 ml). The stirred reaction mixture was then heated to 90° C. (thermostatically controlled heating mantle) for 22 hours. The reaction mixture was then allowed to cool to room temperature and was filtered through a plug of Celite. The reaction flask and the Celite were then washed with ethyl acetate (250 ml). The organic solution was then transferred to a separatory funnel and extracted with additional ethyl acetate (3×200 ml). The combined ethyl acetate solution was then washed with water (2×100 ml), saturated sodium chloride (2×100 ml), dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to give a crude product. This material was triturated with diethylether to give a solid which was filtered off, washed with ether to give 6.82 g of tert-butyl 4-((3-methyl-4-nitrophenoxy)methyl)piperidine-1-carboxylate (yield=78%). 1H-NMR (400 MHz, DMSO-d6) δ 8.06 (d, 1H), 8.64 (d, 1H), 8.62 (s, 1H), 3.9 (s, 2H), 3.34 (m, 4H), 2.00 (m, 1H), 1.46 (m, 1.46), 1.42 (s, 9H). MS (EI): 351 (MH+).

Provenance & Evidence