Water → 2-[2-(3,4-Dichlorophenyl)morpholin-2-YL]ethanol

Participants

Reaction Steps

7.80 g (15.9 mmole) of 2-[4-t-butoxycarbonyl-2-(3,4-dichlorophenyl)morpholin-2-yl]ethanol t-butyldimethylsilyl ether [prepared as described in step (c) above] were dissolved in 150 ml of methylene chloride and 7.05 g (35.5 mmole) of B-bromocatecholborane were added. The mixture was then stirred under a stream of nitrogen at room temperature for 2 hours. At the end of this time, 150 ml of water were added to the reaction mixture, and the mixture was then stirred for a further 2 hours. The reaction mixture was made basic by adding a 1 N aqueous solution of sodium hydroxide. It was then extracted with methylene chloride and the extract was washed with a saturated aqueous solution of sodium chloride. The organic extract was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 19:1 to 17:3 by volume as the eluent, to obtain 4.40 g of the title compound.

Provenance & Evidence