Triethylamine → HCID 19888384, compound

Temperature

0 °C

Methanesulfonyl chloride (14.3 g, 125 mmol) was slowly added to a solution of N-diphenylmethyl azetidin-3-ol (20.0 g, 83.7 mmol) and triethylamine (15.2 g, 151 mmol) in methylene chloride (160 mL) which was maintained at 0° C. by an ice-water bath. After 1.5 hours the slurry was diluted with methylene chloride (160 mL) and ice-water (160 mL). The layers were separated and the organic layer was washed with an ice-water mixture (160 mL), dried (MgSO4), and concentrated in vacuo. A solution of the crude mesylate in dimethylformamide (100 mL) was added dropwise to a slurry of the sodium salt of 2,6-dimethylphenol in dimethylformamide prepared by adding a solution of 2,6-dimethylphenol (15.0 g, 125 mmol) in dimethylformamide to a slurry of sodium hydride (60% oil dispension, 7.20 g, 150 mmol) which had been washed (3×60 mL) with hexane and diluted with dimethylformamide (130 mL). The reaction mixture was warmed at 50° for 42 h, cooled to room temperature and added to 1400 mL of an ice-water mixture. The aqueous slurry was extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with water (100 mL), saturated aqueous sodium chloride (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was chromatographed (silica gel, flash chromatography) eluting with ether/hexane (1:9) to give 15.0 g (52%) of white solid with a melting point of 99°-100° C.

1. customThe layers were separated
2. washthe organic layer was washed with an ice-water mixture (160 mL)
3. dry with materialdried (MgSO4)
4. concentrationconcentrated in vacuo
5. additionA solution of the crude mesylate in dimethylformamide (100 mL) was added dropwise to a slurry of the sodium salt of 2,6-dimethylphenol in dimethylformamide
6. customprepared
7. washhad been washed (3×60 mL) with hexane
8. additiondiluted with dimethylformamide (130 mL)
9. temperatureThe reaction mixture was warmed at 50° for 42 h
10. temperaturecooled to room temperature
11. additionadded to 1400 mL of an ice-water mixture
12. extractionThe aqueous slurry was extracted with ethyl acetate (3×200 mL)
13. washThe combined organic extracts were washed with water (100 mL), saturated aqueous sodium chloride (100 mL)
14. dry with materialdried (MgSO4)
15. concentrationconcentrated in vacuo
16. customThe residue was chromatographed (silica gel, flash chromatography)
17. washeluting with ether/hexane (1:9)

ORD record

ord-f9eab51edcaf4e98b0709b94c470a2c4

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05130309