Triacetoxyperiodinane → (1S,2S,5R)-2-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

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Reaction Steps

Dess-Martin periodinane (3.18 mmol) is added to a solution of (1S,2S,5R)-2-Hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3.24 mmol) in DCM (45 mL, saturated with water). Additional periodinane (0.80 mmol) is added after 2 h. After additional 2.5 h a sat. NaHCO3 solution is added, the layers are separated and the organic layer is washed with aq. Na2S2O3 solution. The aq. layer is extracted twice with DCM, the combined organic layers are concentrated in vacuo and the residue is purified by FC (pentane to pentane/ether 4/1) to give the desired product.

Provenance & Evidence