Dimethylacetamide → HCID 57428868, compound

Participants

Reaction Conditions

Reaction Steps

1-(Thiophen-2-ylsulfonyl)piperidine (5 g, 21.6 mmol) was taken up in anhydrous tetrahydrofuran (90 mL) and the solution, which was kept under a nitrogen atmosphere, was cooled down to −78° C. n-Butyllithium (2.5 M in hexanes, 12.96 mL, 32.4 mmol) was added to the reaction dropwise with a syringe. The reaction was stirred at −78° C. for 10 min and allowed to warm up to −30° C. and stirred for 30 min. The reaction was cooled back down to −78° C. and N,N-dimethylacetamide (4.01 mL, 43.2 mmol) diluted with anhydrous tetrahydrofuran (10 mL) was added slowly to the reaction. The reaction was stirred for 15 min and then allowed to warm up to room temperature over 1 h. The mixture was quenched with acetic acid (10 mL) and diluted with ethyl acetate and a saturated solution of sodium bicarbonate. The layers were separated and the organic layer washed with water and brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 10 to 40% ethyl acetate in hexanes to afford an off-white solid (1.8 g).

Provenance & Evidence