Monobenzone → (+/-)cis-1-(4Benzyloxyphenoxy)-2-tert-butoxycarbonylaminoindane

Participants

Reaction Steps

The title compound was prepared in a similar manner to Preparation 18 from (±) N-tert-butoxycarbonyl-1,2-iminoindane (5 g, 21.6 mmol), 4-benzyloxyphenol (4.3 g, 21.6 mmol), pyridinium p-toluenesulfonate (100 mg) and chloroform (150 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (100 ml) then washed sequentially with water and brine. After drying over sodium sulfate, volatiles were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford a light brown solid which was recrystallised to afford the title compound (3.6 g) as a white solid. (from diethyl etherhexanes).

Provenance & Evidence