Epibromohydrin → HCID 59207183, compound

To a stirring solution of C—((R)-6-iodo-1,2,3,4-tetrahydro-naphthalen-1-yl)-methylamine (0.79 g, 2.75 mmol) in isopropanol (6 mL) at ice bath temperature and under nitrogen atmosphere, was added dropwise epibromohydrin ((0.38 g, 2.8 mmol). The ice bath was removed and the reaction mixture was stirred for 18 hours at room temperature. Triethylamine ((0.39 mL, 2.8 mmol) was added, and the reaction mixture was stirred at room temperature for two hours, then at 60° C. for three hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was taken up in EtOAc. The EtOAc solution was washed with water and 0.5 M aqueous sodium carbonate, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting oil was chromatographed by HPLC (hexanes/EtOAc 1:1 to 50% hexanes/27% EtOA/15% MeOH/8% con. NH4OH) to 0.5 g (53%) of 1-((R)-6-Iodo-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-azetidin-3-ol, MS M+H=344

1. customThe ice bath was removed
2. additionTriethylamine ((0.39 mL, 2.8 mmol) was added
3. stirringthe reaction mixture was stirred at room temperature for two hours
4. waitat 60° C. for three hours
5. temperatureThe reaction mixture was cooled to room temperature
6. concentrationconcentrated under reduced pressure
7. washThe EtOAc solution was washed with water and 0.5 M aqueous sodium carbonate
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe resulting oil was chromatographed by HPLC (hexanes/EtOAc 1

ORD record

ord-9a34bc489abc4ee289540959d01c5fd2

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07671235B2