Triethylamine → HCID 66962074, compound

Triethylamine (0.135 ml, 0.958 mmol) and 60 μl (0.760 mmol) of methanesulphonyl chloride were added to a solution of 70.5 mg (0.377 mmol) of 4-bromobenzylalcohol in dichloromethane (2 ml) under ice cooling, and the mixture was stirred for 1.5 hr. The reaction solution was diluted with 10 ml of ethyl acetate, and the diluted solution was washed with an 8% aqueous sodium hydrogencarbonate solution. The aqueous layer was extracted twice with 3 ml of ethyl acetate. The organic layers were combined, were washed with 25% brine, and were dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under the reduced pressure. The residue was dissolved in 1.8 ml of N,N-dimethylformamide, 87 μl of 2,5-dihydro-1H-pyrrole (70% purity, 0.793 mmol) was added to the solution, and the mixture was stirred at 80° C. for 3 hr. The reaction solution was diluted with 10 ml of ethyl acetate, and the diluted solution was washed thrice with 5 ml of water. The aqueous layer was extracted twice with 5 ml of ethyl acetate. The organic layers were combined, were washed with 25% brine, and were dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under the reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform:methanol=18:1) to give 63.8 mg (yield 71%) of the title compound.

1. washthe diluted solution was washed with an 8% aqueous sodium hydrogencarbonate solution
2. extractionThe aqueous layer was extracted twice with 3 ml of ethyl acetate
3. washwere washed with 25% brine
4. dry with materialwere dried over anhydrous sodium sulfate
5. filtrationfollowed by filtration
6. concentrationThe filtrate was concentrated under the reduced pressure
7. dissolutionThe residue was dissolved in 1.8 ml of N,N-dimethylformamide
8. stirringthe mixture was stirred at 80° C. for 3 hr
9. washthe diluted solution was washed thrice with 5 ml of water
10. extractionThe aqueous layer was extracted twice with 5 ml of ethyl acetate
11. washwere washed with 25% brine
12. dry with materialwere dried over anhydrous sodium sulfate
13. filtrationfollowed by filtration
14. concentrationThe filtrate was concentrated under the reduced pressure
15. customthe residue was purified by preparative thin-layer chromatography (chloroform:methanol=18:1)

ORD record

ord-b830c93a7ee3413dbe3a2f97efc838d1

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879808B2