Aluminium lithium hydride → (R)-N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine

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Reaction Steps

In 50 mL of dry toluene, 2.0 g (5.8 mmol) of (R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate and 1.5 g (41 mmol) of lithium aluminum hydride were combined and gently refluxed for 24 h. Next the mix was quenched with 5 g of sodium sulfate decahydrate and allowed to stir for 2 h. The mix was then filtered over celite and the pad was washed with ethyl acetate several times. The filtrate was then concentrated and the crude was purified on silica using 0 to 5% MeOH (10% ammonium hydroxide) in ethyl acetate to give the product. MS 259 (ESI, pos. ion).

Provenance & Evidence