Ethyl Acetate → HCID 59401353, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methoxynaphthalene-1-ylmethyl(3-methylbutyl)amine (Preparation 13) (310 mg, 1.20 mmol) in DCM (15 mL) at −78° C., was added 1M BBr3 in DCM (3.61 mL, 3.61 mmol.). The reaction mixture was stirred at −78° C. for 16 h. NaHCO3 (0.5 mL) was added and the mixture partitioned between NaHCO3 (0.25 mmol) and EtOAc (50 mL). The aqueous phase was extracted with EtOAc (2×50 mL) and the combine organic phases washed with 1M NaOH (20 mL). The aqueous phase was acidified with 1M HCl to pH 7 and extracted with EtOAc (100 mL). The organic phase was washed with brine (25 mL) and dried (MgSO4). Solvent was removed in vacuo to give the title compound: RT=2.49 min; m/z (ES+)=244.1 [M+H]+.

Provenance & Evidence