Chloromethyl Methyl Ether → tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate

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Reaction Steps

To a solution of 1 g of tert-butyl[(1R,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]carbamate in 10 ml of THF was added 16.9 ml of a 0.5 M potassium hexamethyldisilazane/toluene solution at −78° C., followed by stirring for 30 minutes. 0.92 ml of chlorodimethyl ether was added thereto at −78° C., followed by warming to room temperature for 3 hours. 4 ml of a 0.5 M potassium hexamethyldisilazane/toluene solution and 0.31 ml of chlorodimethyl ether were added thereto at −78° C., followed by stirring at room temperature for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 311 mg of tert-butyl [(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate.

Provenance & Evidence