2-Chlorobenzenesulfonyl chloride → (R)-Methyl 3-(2-chloro-N-methylphenylsulfonamido)-2,3-dihydro-1H-indene-5-carboxylate

TEA (864 μl, 6.23 mmol, 2.5 eq.) was added to a cooled (0° C.) solution of (R)-methyl 3-(methylamino)-2,3-dihydro-1H-indene-5-carboxylate (A-17) (2.49 mmol, 1.0 eq.) in methylene chloride (10 ml) and the reaction mixture was allowed to stir for 15 min. A solution of 2-chlorobenzene-1-sulfonyl chloride (407 μl, 2.99 mmol, 1.2 eq.) in methylene chloride (5 ml) was then added and the reaction mixture was stirred at RT for 4 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with methylene chloride (100 ml) and the organic layer was washed with water (50 ml) and brine (50 ml), and dried over anhydrous Na2SO4. The solvent was evaporated to afford the crude product which was purified by column chromatography (silica gel; 20% ethyl acetate/hexanes) to yield the desired compound as a white solid. Yield: 89% (840 mg, 2.216 mmol).

1. stirringthe reaction mixture was stirred at RT for 4 h
2. customAfter completion of the reaction (monitored by TLC)
3. washthe organic layer was washed with water (50 ml) and brine (50 ml)
4. dry with materialdried over anhydrous Na2SO4
5. customThe solvent was evaporated
6. customto afford the crude product which
7. customwas purified by column chromatography (silica gel; 20% ethyl acetate/hexanes)

ORD record

ord-1de39b5fc7b34c8786839432f1260565

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2