Boron tribromide → HCID 53977496, compound

Participants

Reaction Steps

A solution of the (1R)-1-(3-chlorophenyl)-2-[3-(3-methoxyphenyl) cyclohexylamino]ethanol (trans-H) obtained in Example 3 (2.21 g) in methylene chloride (100 ml) was cooled to -10° C. After slowly adding dropwise a solution of 1 M boron tribromide in methylene chloride thereto, the mixture was stirred for 2 hours while gradually heating it to room temperature. The reaction solution was poured a portion at a time into an aqueous sodium bicarbonate solution while cooling on ice in order to terminate the reaction, and the extraction was performed with a mixed solvent of chloroform:ethanol=5:1. After washing the organic layer with saturated saline, it was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to produce a crude product which was then separated and purified by silica gel column chromatography (chloroform-chloroform:methanol=20:1) to give 1.72 g of (1R)-1-(3-chlorophenyl)-2-[3-(3-hydroxyphenyl)cyclohexylamino]ethanol (trans-H) (81.1% yield).

Provenance & Evidence