Water → HCID 59401291, compound

Participants

Reaction Steps

To a solution of 5-methoxynaphthalen-1-ylmethylamine (Preparation 12) (389 mg, 2.08 mmol) in MeOH (15 mL), was added 3-methylbutyraldehyde (223 μL, 2.08 mmol). The mixture was stirred for 16 h at rt under nitrogen before adding NaBH4 (236 mg, 6.24 mmol). After stirring for 1 h water (0.5 mL) was added and the solvent removed in vacuo. The mixture was partitioned between EtOAc (100 mL) and NaHCO3 (25 mL), the organic phase was washed with water (25 mL), brine (25 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (DCM: MeOH: NH4OH, 97:3:0.3 to 95:5:0.5) to give the title compound: RT=2.46 min; m/z (ES+)=258.1 [M+H]+.

Provenance & Evidence