1(2H)-Naphthalenone, 3,4-dihydro-2-((dimethylamino)methyl)- → (1RS,2RS)-2-Dimethylaminomethyl-1-(3-methoxybenzyl)-1,2,3,4-tetrahydro-naphth-1-ol

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Reaction Steps

A solution of 8.13 g 2-dimethylaminomethyl-3,4-dihydro-naphthalen-1-one in 20 ml dry diethyl ether was added dropwise to a freshly prepared Grignard reagent of 1.46 g magnesium filings and 8.8 ml 3-methoxybenzyl chloride in 50 ml dry diethyl ether at 20° C., while stirring. The reaction mixture was heated under reflux for 3 hours, decomposed by dropwise addition of 30 ml of a saturated ammonium chloride solution and, after dilution with distilled water, extracted three times with 50 ml diethyl ether each time. The extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography with ethyl acetate/methanol=20/1 as the eluting agent. 9.41 g (72.3% of th.) of the title compound were obtained here as a diastereomer mixture.

Provenance & Evidence