Water → N-(4-(methoxymethoxy)butyl)benzenesulfonamide

4-Aminobutanol (700 mg) was dissolved in THF (12.5 mL). To the solution, magnesium oxide (1.58 g), water (3.2 mL), and benzenesulfonyl chloride (1.15 mL) were added, and the mixture was stirred at room temperature for 2 hours. The precipitate was removed by filtration, and washed with chloroform (50 mL). Then, the combined filtrate was concentrated under reduced pressure. To the residue, water (20 mL) was added, and the resultant mixture was then extracted with ethyl acetate (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100% ethyl acetate). The obtained colorless oil (1.48 g) was dissolved in dichloromethane (7.5 mL). To the solution, N,N-diisopropylethylamine (3.43 mL) and chloromethyl methyl ether (1.0 mL) were added, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (50% ethyl acetate/hexane) to obtain the title compound (1.36 g) as a colorless oil.

1. customThe precipitate was removed by filtration
2. washwashed with chloroform (50 mL)
3. concentrationThen, the combined filtrate was concentrated under reduced pressure
4. additionTo the residue, water (20 mL) was added
5. extractionthe resultant mixture was then extracted with ethyl acetate (20 mL)
6. washThe organic layer was washed with brine (20 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (100% ethyl acetate)
10. dissolutionThe obtained colorless oil (1.48 g) was dissolved in dichloromethane (7.5 mL)
11. additionTo the solution, N,N-diisopropylethylamine (3.43 mL) and chloromethyl methyl ether (1.0 mL) were added
12. stirringthe mixture was stirred at room temperature for 1.5 hours
13. concentrationThe reaction mixture was concentrated under reduced pressure
14. customthe residue was then purified by silica gel column chromatography (50% ethyl acetate/hexane)

ORD record

ord-affdcf1ff0e949dabdf9591d588d7cf2

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530490B2