Sodium Thiosulfate → HCID 86730722, compound

Temperature

0 °C

Dess-Martin periodinane (162 mg, 0.38 mmol, 2.0 eq) is added dropwise at 0° C. to a stirred solution of (3R,6S)-[6-(2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (47 mg, 0.19 mmol, 1.0 eq) in dichloromethane (3 mL). The reaction mixture is stirred 0° C. for 30 minutes then at room temperature for 1 hour. Then a saturated sodium thiosulfate aqueous solution (2 mL) is added, followed by a saturated sodium hydrogen carbonate aqueous solution (2 mL). The resulting mixture is stirred for 30 minutes and extracted with dichloromethane (3×10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 10:1 to 1:1, v/v) to afford (3R,6S)-[6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester as a white solid (20 mg, 43% yield).

1. waitat room temperature for 1 hour
2. stirringThe resulting mixture is stirred for 30 minutes
3. extractionextracted with dichloromethane (3×10 mL)
4. dry with materialThe combined organic layers are dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a crude product that
8. customis purified by column chromatography (silica gel, eluent

ORD record

ord-fadf66f965cf41dea81b221b0e3516c3

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321788B2