Sulfur tetrafluoride → HCID 19807375, compound

4.8 g (25 mmol) of N-(3-aminoxy-2-hydroxypropyl)-methylamine dihydrochloride are dissolved at -78° in 80 g of liquid hydrogen fluoride in a Teflon autoclave. 5.6 g of sulfur tetrafluoride are introduced and the vessel is closed and left to stand for 24 hours at room temperature. After degassing, the residue is dissolved in 2N hydrochloric acid. This solution is filtered and the filtrate is neutralised, in portions, with solid sodium hydrogen carbonate; a solution of 13 g of di-tert-butyl dicarbonate in 50 ml of tetrahydrofuran is added and the mixture is left to stand for 1 hour. The reaction mixture is diluted with 200 ml of ether and the organic phase is separated off, washed with water, dried over magnesium sulfate, filtered and concentrated by evaporation. The oil that remains behind is chromatographed with a mixture of hexane:ethyl acetate 3:1 over 500 g of silica gel, yielding the starting compound in the form of a yellow oil, Rf value 0.18.

1. customthe vessel is closed
2. waitleft
3. customAfter degassing
4. dissolutionthe residue is dissolved in 2N hydrochloric acid
5. filtrationThis solution is filtered
6. additiona solution of 13 g of di-tert-butyl dicarbonate in 50 ml of tetrahydrofuran is added
7. waitthe mixture is left
8. waitto stand for 1 hour
9. additionThe reaction mixture is diluted with 200 ml of ether
10. customthe organic phase is separated off
11. washwashed with water
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated by evaporation
15. customThe oil that remains behind is chromatographed with a mixture of hexane:ethyl acetate 3:1 over 500 g of silica gel
16. customyielding the starting compound in the form of a yellow oil, Rf value 0.18

ORD record

ord-74225ddd281445a4853f7fb8c6c6c154

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05169867