(1S,3S,4S)-4-azido-N,N-dibenzyl-3-methylcyclohexanamine (1R,3R,4R)-4-azido-N,N-dibenzyl-3-methylcyclohexanamine → (1S,3S,4S)-N1,N1-dibenzyl-3-methylcyclohexane-1,4-diamine (1R,3R,4R)-N1,N1-dibenzyl-3-methylcyclohexane-1,4-diamine

Participants

Reaction Steps

To a solution of (1S,3S ,4S)-4-azido-N,N-dibenzyl-3-methylcyclohexanamine/(1R,3R,4R)-4-azido-N,N-dibenzyl-3-methylcyclohexanamine (2.174 g, 6.5 mmol) in acetic acid (50 mL) was added slowly Zn-dust (0.638 g, 9.75 mmol). The mixture was stirred for 30 min at ambient temperature. Additional Zn-dust was added (150 mg) and stirring was continued for ˜15 min. The mixture was diluted carefully with 1N aqueous HCl and diethylether. The separated aqueous layer was extracted with diethylether (5ט100 mL). The aqeuous layer was partially lyophilized and concentrated to dryness in vacuo. The resulting residue was diluted with 1N aqueous HCl and concentration to dryness was repeated. Dilution with 1N HCl and concentration was repeated. The resulting residue was dissolved in water/acetonitrile and lyophilized to provide crude (1S,3S ,4S)—N1,N1-dibenzyl-3-methylcyclohexane-1,4-diamine/(1R,3R,4R)—N1,N1-dibenzyl-3-methylcyclohexane-1,4-diamine as fluffy white solid. The crude material was directly used in the next step without further purification. Yield: 2.292 g. LCMS (m/z): 309.3 [M+H]+; Retention time=0.50 min.

Provenance & Evidence