Triacetoxyperiodinane → HCID 86590604, compound

Participants

Reaction Steps

Dess-Martin reagent (90 mg, 0.21 mmol) is added to an ice cold solution of 6-[(Naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid (1-hydroxymethyl-3-methanesulfonylamino-3-oxo-propyl)-amide (48 mg, 0.09 mmol) in CH2Cl2 (5 mL). The solution is stirred at 0 C. for 2 h and treated with saturated NaHCO3. The resulting solution is extracted with EtOAc and the combined organic extracts are washed with brine, dried (Na2SO4), filtered, and concentrated. The crude residue obtained is purified by flash chromatography on silica gel (CH2Cl2/MeOH) to yield 27 mg of product as a mixture of diastereomers. MS (ESI) 555 (M+1).

Provenance & Evidence