Phenyl thioxochloroformate → HCID 86598923, compound

Participants

Reaction Steps

To a solution of 2-tert-butyl 3-methyl (1R,3S,4S, 6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (4.5 g) in pyridine (10 mL), was added O-phenyl chlorothiocarbonate (3.15 g). The mixture was then stirred at room temperature for 3 hrs. The resulting mixture was evaporated in vacuo. To the residue, water was added. The mixture was extracted with ethyl acetate. The combined organic phase was washed successively with diluted hydrochloric acid, sodium hydrogen carbonate solution and brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (2:1) to give the target compound (5.22 g).

Provenance & Evidence