Acetic Acid → HCID 58218363, compound

A colorless oil (285 mg) was obtained according to the method of Reference Example 233 from 4-aminobutanol (89 mg) and 3-benzoyloxybenzenesulfonyl chloride (300 mg) obtained according to a method described in the document (J. Pesticide. Chem., 13, 107-115 (1988)). This oil was dissolved in methanol (5.0 mL). To the solution, DBU (441 mg) was added, and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, acetic acid (210 μL) was added, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100% ethyl acetate). The obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL). To the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added, and the mixture was stirred at 90° C. for 14 hours. The reaction mixture was cooled to room temperature, water (10 mL) was then added thereto, and the resultant mixture was then extracted with ethyl acetate (10 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to obtain the title compound (91 mg) as a colorless oil.

1. customobtained
2. stirringthe mixture was stirred at room temperature for 10 minutes
3. concentrationThe reaction mixture was then concentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (100% ethyl acetate)
5. dissolutionThe obtained colorless oil (147 mg) was dissolved in DMF (4.0 mL)
6. additionTo the solution, potassium carbonate (141 mg), potassium iodide (8.5 mg), and (chloromethyl)cyclopropane (47 μL) were added
7. stirringthe mixture was stirred at 90° C. for 14 hours
8. temperatureThe reaction mixture was cooled to room temperature
9. additionwater (10 mL) was then added
10. extractionthe resultant mixture was then extracted with ethyl acetate (10 mL)
11. washThe organic layer was washed with water (10 mL) and brine (10 mL)
12. dry with materialdried over anhydrous sodium sulfate
13. concentrationconcentrated under reduced pressure
14. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

ORD record

ord-b80ad4076d574308a1f8e579841dcda6

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530490B2