Sodium Azide → 3-Azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

Referring to Scheme 2, acylation of the alpha-tetralone 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one (Compound 1) with diethylcarbonate was followed by reduction with triethylsilane to give 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid ethyl ester (Compound 10). Reduction and conversion to 3-bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 12) is followed by alkylation with sodium azide in DMF to give 3-azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 13). Chiral separation of Compound 13 is followed by hydrogenation to give a compound of the invention, C-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-methylamine (Compound 14). Alternatively, reduction and conversion to 3-bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene (Compound 12) is followed by alkylation with substituted amines to give 1-phenyl-3-aminoalkyl-1,2,3,4-tetrahydronaphthalenes (Compound 15).

Provenance & Evidence