Triethylamine → HCID 21914292, compound

1-(2-Bromophenyl)pyrrolidin-3-ol (1 g) was stirred in toluene (30 ml). Triethylamine (0.69 ml) was added and the solution was cooled in an ice-bath. Methane sulphonyl chloride (0.38 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature over 2 h and stirred for a further 2.5 h. The mixture was filtered, washed through with toluene and the filtrate concentrated to ca. 20 ml in vacuo. Morpholine (10 ml) was then added and the solution stirred at room temperature overnight, a further portion of morpholine (10 ml) was added and the solution was heated at reflux for 24 h. Volatile materials were then removed in vacuo, the residue was diluted with water (40 ml) and extracted with diethyl ether (3×20 ml). The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was triturated with isohexane/diethyl ether and product collected by filtration as a yellow solid (0.93 g).

1. temperaturethe solution was cooled in an ice-bath
2. filtrationThe mixture was filtered
3. washwashed through with toluene
4. concentrationthe filtrate concentrated to ca. 20 ml in vacuo
5. additionMorpholine (10 ml) was then added
6. stirringthe solution stirred at room temperature overnight
7. additiona further portion of morpholine (10 ml) was added
8. temperaturethe solution was heated
9. temperatureat reflux for 24 h
10. customVolatile materials were then removed in vacuo
11. additionthe residue was diluted with water (40 ml)
12. extractionextracted with diethyl ether (3×20 ml)
13. washThe combined extracts were washed with brine
14. dry with materialdried (MgSO4)
15. filtrationfiltered
16. customevaporated
17. customThe residue was triturated with isohexane/diethyl ether and product
18. filtrationcollected by filtration as a yellow solid (0.93 g)

ORD record

ord-8e7da4f21d0643f2b79cbf3db8f4e4f6

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956084B2