Dimethylacetamide → HCID 57428868, compound

Temperature

-78 °C

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).

1. additionwas added to the reaction dropwise with a syringe
2. temperatureto warm up to −30° C.
3. stirringstirred for 30 min
4. additionwas added slowly to the reaction
5. stirringThe reaction was stirred for 15 min
6. temperatureto warm up to room temperature over 1 h
7. customThe mixture was quenched with acetic acid (10 mL)
8. additiondiluted with ethyl acetate
9. customThe layers were separated
10. washthe organic layer washed with water and brine
11. dry with materialThe organic layer was then dried with sodium sulfate
12. concentrationconcentrated
13. custompurified by flash chromatography

ORD record

ord-9ac155b06694493fac7a4d0c0f362814

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2