Ammonium Chloride → (1R,2S,6R)-2-azido-6-[tert-butyl(dimethyl)silyl]oxy-cyclohexanol

Temperature

60 °C

To a stirred solution of tert-butyl-dimethyl-[[(1R,5R,6R)-5-methyl-7-oxabicyclo[4.1.0]heptan-5-yl]oxy]silane, 50c, (0.05 g, 2.15 mmol) in methanol (5 mL) and H2O (0.6 mL) was added NH4Cl (0.23 g, 0.15 mL, 4.30 mmol), followed by portion wise addition of sodium azide (0.42 g, 1.26 mL, 6.45 mmol). The resulting reaction mixture was warmed to 60° C., stirred for 12 h, at which point TLC-analysis revealed traces of the starting material. The reaction mixture was cooled to ambient temperature, quenched with H2O (2 mL), concentrated under reduced pressure to remove methanol, extracted with ethyl acetate (3×15 mL), washed with brine (10 mL), dried over MgSO4, filter and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (2.5-10% ethyl ether in hexanes gradient) to afford 254 mg of (1R,2S,6R)-2-azido-6-[tert-butyl(dimethyl)silyl]oxy-cyclohexanol, 50d, as a clear oil.

1. customThe resulting reaction mixture
2. temperatureThe reaction mixture was cooled to ambient temperature
3. customquenched with H2O (2 mL)
4. concentrationconcentrated under reduced pressure
5. customto remove methanol
6. extractionextracted with ethyl acetate (3×15 mL)
7. washwashed with brine (10 mL)
8. dry with materialdried over MgSO4
9. filtrationfilter
10. concentrationconcentrated under reduced pressure
11. customThe crude product was purified by silica gel chromatography (2.5-10% ethyl ether in hexanes gradient)

ORD record

ord-5ea788cac59d4cfaa53a155045b4b110

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345708B2