Triethylsilane → HCID 67458539, compound

Participants

Reaction Conditions

Reaction Steps

In a nitrogen stream, triethylsilane (0.21 mL, 1.22 mmol) was added dropwise to a solution of (2R,3S,4R,5R)-2,3,4-trisbenzyloxy-5-benzyloxymethyl-1-[1-(4-ethylbenzyl)-1H-indol-3-yl]cyclohexanol (469 mg, 0.61 mmol) in methylene chloride (6 mL) at 0° C. A boron trifluoride-diethyl ether complex (0.093 mL, 0.73 mmol) was added dropwise thereto over five minutes and the reaction mixture was stirred at 0° C. for two hours. A saturated sodium hydrogencarbonate aqueous solution was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:15)] to obtain the title compound (232 mg, 51%).

Provenance & Evidence