Water → HCID 68286080, compound

Temperature

25 °C

tert-butyl amine [8.5 g, 12.32 ml, 116.0 mmol) was added dropwise to a stirred suspension of 4-bromo-5,6,7,8-tetrahydronaphthalene-1-sulfonyl chloride (59a, 12.0 g, 38.8 mmol) in 150 ml tetrahydrofuran at 0° C. The reaction mixture was then stirred at a temperature of about 25° C. for 2 hours. The progress of the reaction was monitored by TLC. Water (100 ml) was added to the reaction mixture, and the mixture so obtained was extracted with ethyl acetate (2×150 ml). The combined organic layer was then dried over sodium sulphate, and the dried organic layer was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 15% ethyl acetate in hexanes as an eluent to obtain the title compound (2.34 g, 17.4%).

1. customthe mixture so obtained
2. extractionwas extracted with ethyl acetate (2×150 ml)
3. dry with materialThe combined organic layer was then dried over sodium sulphate
4. concentrationthe dried organic layer was concentrated under reduced pressure
5. customto obtain a crude product, which
6. customwas then purified by column chromatography over silica gel (100-200 mesh)

ORD record

ord-fb2c6202d20848e1834755d4e1c76ab2

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2