Water → racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Racemic 6-azido-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (28 mg, 0.13 mmol) was dissolved in THF (1253 mL) and water (66.0 mL) at 0° C. To this solution was added sodium borohydride (6.49 mg, 0.17 mmol). The resulting solution was stirred at 0° C. for 45 min. After that, the reaction was quenched by several drops of 1N HCl. The mixture was loaded to an ISCO 13 g column directly and purified by ISCO Combiflash Companion (10% ethyl acetate-hexane for 3 min then ramp to 50% ethyl acetate-hexane over 7 min then 20% ethyl acetate-hexane for 5 more min, product came out 8-10 min) to afford racemic (5S*,6R*)-6-azido-5-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (15.0 mg, 0.07 mmol, 53.1%) as a white solid. NMR showed that the product was a mixture of around 6:1 two diastereomers; LCMS=215.22 [M+H]+.

Provenance & Evidence