Hydrochloric Acid → Racemic 4-(2-formyl-4-iodo-phenoxy)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-hydroxy-5-iodo-benzaldehyde (Aldrich, 4.96 g, 20 mmol) in DMF (80 mL), potassium carbobate (10 g, 60 mmol) and 7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (8 g, 40 mmol) were added and the mixture was stirred at 70° C. for three days and 80° C. for two days. The mixture was poured into 1N HCl and the mixture was extracted with EtOAc (3×50 mL). The extracts were combined and dried over sodium sulfate and concentrated to give an oil, which was chromatographied on an ISCO machine (10-30% EtOAc/Hexanes) to yield an oil, 3.4 g. MS (H+), 348.

Provenance & Evidence