m-Chloroperbenzoic acid → HCID 86668244, compound

(1R,6R)-6-Azidocyclohex-3-en-1-ol 3c (500 mg, 3.60 mmol) was dissolved in 150 mL of dichloromethane followed by the addition of sodium bicarbonate (600 mg, 7.20 mmol) and m-Chloroperbenzoic acid (2.40 g, 9.60 mmol), the reaction solution was stirred for 12 hours. The resulting solution was washed with saturated sodium bicarbonate solution (50 mL), saturated sodium thiosulfate solution (50 mL) and saturated sodium chloride solution (50 mL×3) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure, the residue was purified by HPLC to obtain the title compound (1S,3R,4R)-4-azido-7-oxabicyclo[4.1.0]heptan-3-ol 3d (360 mg, yield: 64.6%) as a white solid.

1. washThe resulting solution was washed with saturated sodium bicarbonate solution (50 mL), saturated sodium thiosulfate solution (50 mL) and saturated sodium chloride solution (50 mL×3) successively
2. dry with materialdried over anhydrous magnesium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customthe residue was purified by HPLC

ORD record

ord-696f71f436734fd1a45a5afc27119522

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691822B2