Sodium Hydroxide → (2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester

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Reaction Steps

A solution of 114 mg (o.30 mmol) {2-[(5-Vinyl-benzofuran-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (57), 5 ml THF and 1.4 ml of a 0.5M solution of 9-BBN in THF was stirred at rt for 4 h. A solution of 86 mg NaOH in 0.6 ml water was added and stirring was continued for further 2 h. The reaction mixture was washed with brine and the organic phase dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethylacetate 1:1) to give 54 mg (0.136 mmol) (2-{[5-(2-Hydroxy-ethyl)-benzofuran-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester (58).

Provenance & Evidence