1-Tetralone → (+/-) Cis 4-azido-1,2,3,4-tetrahydro-naphthalen-1-ol

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Reaction Steps

A solution of 1-tetralone (2.92 g, 20 mmol), N-bromosuccinimide (3.56 g, 20 mmol) and azodibutyronitrile (80 mg) in carbon tetrachloride (80 mL) was refluxed for 1.25h, then evaporated in vacuo. The resulting oil was dissolved in DMF (8 mL), treated with sodium azide (2.6 g, 40 mmol) and stirred at RT for 2h. The reaction mixture was partitioned between Et2O (200 mL) and H2O (50 mL). The resulting organic layer was dried (MgSO4), filtered and evaporated in vacuo. The resulting oil was dissolved in EtOH (100 mL), cooled to 0° C. under argon and treated with sodium borohydride (0.76 g, 20 mmol). The reaction mixture was stirred at RT for 1h, concentrated in vacuo to approx. 50 mL and partitioned between H2O and Et2O. The aqueous layer was extracted with DCM (100 mL) and EtOAc (100 mL) and the combined organic layers were dried (MgSO4), filtered, concentrated in vacuo and purified by FCC using 0-30% cyclohexane/diethyl ether to give the title compound at Rf 0.2 as a dark red oil (1.5 g, 40%). 1H NMR (300 MHz, CDCl3): 7.57-7.52 (1 H, m), 7.43-7.28 (3 H, m), 4.81-4.72 (1 H, m), 4.55-4.49 (1 H, m), 2.13-1.99 (3 H, m), 1.79 (1 H, m).

Provenance & Evidence