Formic Acid → 2,2,2-Trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

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Reaction Steps

Purge a 100 ml round bottom flask containing 0.50 g (1.95 mmol) of (R)-2,2,2-trifluoro-N-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide and 0.062 g (0.098 mmol) RuCl[(R,R)-Tsdpen(p-cymene)] with argon (catalyst prepared using procedure from Org Syn, Vol 82, pg 10-17, note 5). Add 25 ml of dry DMF by syringe and stir. To this solution was added a mixture of 0.43 ml (3.11 mmol) of triethylamine and 0.12 ml (3.11 mmol) of HCOOH. The reaction mixture was stirred at 50° C. overnight. To complete the reaction, additional RuCl[(R,R)-Tsdpen(p-cymene)] (0.062 g), triethylamine (0.43 ml) and HCOOH (0.12 ml) were added and stirring continued at 50° C. for an additional 6-8 hr. The reaction mixture was cooled to room temp, then diluted with 150 ml EtOAc, and washed with 20 ml distilled water. The organic phase was dried over MgSO4 and concentrated in vacuo, and purified by column chromatography (eluting with 1% MeOH in DCM), to give 0.417 g (83%) of the titled compound.

Provenance & Evidence