1,4-Dioxane → (S)-1-azido-3-phenylpropan-2-amine

Participants

Reaction Steps

A solution of tert-butyl (S)-3-azido-1-phenylpropan-2-ylcarbamate (1.0045 g, 3.6 mmol) was dissolved in 4 M HCl in dioxane (20 mL, 80 mmol) and stirred at rt for 2 h. The solvent was stripped. The residue was taken up in CH2Cl2 (50 mL) and 1 N aq NaOH (10 mL), extracted with CH2Cl2 (3×10 mL), washed with brine (3×5 mL), dried (Na2SO4), decanted, and stripped to afford (S)-1-azido-3-phenylpropan-2-amine (812.9 mg, quant, 80% purity) as a clear oil. MS ESI+ve m/z 177 (M+1).

Provenance & Evidence