3,4-Dichlorophenol → 9-(3,4-Dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Diisopropylazo dicarboxylate (315 mg, 1.56 mmol) in diethyl ether (2 mL) was added slowly to an ice cooled solution of triphenylphosphine (582 mg, 2.22 mmol) in diethyl ether (5 mL). The reaction mixture was stirred for 20 min. 3,4-Dichlorophenol (290 mg, 1.78 mmol) in diethyl ether (2 mL) was added and stirred 30 min at 0° C. and 9-hydroxy-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (400 mg, 1.48 mmol) in diethylether (5 mL) was added and the mixture stirred at room temperature over night. Evaporation followed by flash chromatography (heptane/ethylacetate 9:1) gave 340 mg (56%) of 9-(3,4-dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester.

Provenance & Evidence