Sodium Thiosulfate → HCID 59721733, compound

Participants

Reaction Steps

To a suspension of Dess-Martin periodinane (0.51 g, 0.0012 mol) in anhydrous CH2Cl2 (10 mL) was added a solution of tert-butyl 3-fluorophenethyl(2-hydroxyethyl)carbamate (V-5b, 0.28 g, 0.001 mol) in anhydrous CH2Cl2 (5 mL) via a cannula, and the reaction mixture was stirred at room temperature for 18 h under a N2 atmosphere. Na2S2O3 (1 M, 10 mL) was then added to the reaction mixture. After being stirred for 10 min, the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (15 mL×3). The combined organic layers were washed with 5% aqueous NaHCO3 (20 mL) and brine (20 mL), and dried over Na2SO4. The solvent was evaporated. The residue was then purified by column chromatography (silica gel, hexane:EtOAc=7.5:2.5) to afford a colorless oil (XII-8, 0.24 g, 83%).

Provenance & Evidence