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

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 12 (0.293 g, 0.79 mmol) and sodium azide (0.154 g, 2.38 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between water and EtOAc. The organic layer was separated, washed with water, dried over Na2SO4, and evaporated to give compound 13 as a pale yellow oil (mixture of cis and trans diastereomers, ratio=1:1.1, 0.18 g, 68%). The diastereomers were separated using a preparative chiral HPLC procedure (ChiralPak OD column; hexanes:MeOH=98:2; μ=8 ml/min; and λ=225 nm) to give compounds 13a-13d (retention times: 9.8 min, 12.0 min, 14.5 min and 20.1 min, respectively).

Provenance & Evidence