7-Methoxy-2-tetralone → HCID 69745570, compound

Participants

Reaction Steps

To a solution of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one (1.0 g, 5.67 mmol) and 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (1.34 g, 6.23 mmol) in dichloroethane (50 mL) under a nitrogen atmosphere was added sodium triacetoxyborohydride (3.0 g, 14.2 mmol, 2.5 eq.) in a single portion. The reaction was stirred at room temperature for 24 h. The reaction was concentrated in vacuo and partitioned between EtOAc (100 mL) and 5% aq. KOH (50 mL). The aqueous layer was extracted twice more with ethyl acetate (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. Flash chromatography on silica gel eluting with 5% methanol/methylene chloride afforded 4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester as an oil (2.1 g).

Provenance & Evidence