Sodium Thiosulfate → HCID 86730303, compound

Participants

Reaction Steps

(3R,4S and 3S,4R)-4-Hydroxy-3-methyltetrahydrothiophene-3-carbonitrile (140 mg, 0.98 mmol) was dissolved in DCM (4.9 mL) and was stirred vigorously at ambient temperature. m-CPBA (340 mg, 2.0 mmol) was added in three portions and the resulting mixture was maintained at ambient temperature for 18 hours. The mixture was then diluted with 1M aqueous sodium thiosulfate and extracted with EtOAc. The organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-100% EtOAc/hexanes) to afford the title compound. 1H NMR (600 MHz, CD3OD): δ 4.40 (t, J=6.5 Hz, 1H); 3.70 (d, J=13.6 Hz, 1H); 3.56 (dd, J=13.8, 6.2 Hz, 1H); 3.29-3.30 (m, 1H); 3.23 (dd, J=13.7, 6.8 Hz, 1H); 1.60 (s, 3H).

Provenance & Evidence