Methanol → (1R,4R)-4-(tert-Butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine

Participants

Reaction Steps

To a 250 ml round bottom flask containing 4 g (8.0 mmol) of N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide was added 160 ml of MeOH. To this solution was added a solution of 8.34 g (60 mmol) potassium carbonate in 16 ml of water. The reaction mixture was stirred at room temp overnight. The reaction mixture was diluted with 150 ml EtOAc, and after separation, the aqueous phase was extracted several times with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo to afford 3.09 g (96%) of the title compound, whose purity was good enough to use crude. (Note: On separate occasion, this hydrolysis became sluggish, and 30 ml of 3M NaOH was added, upon which the reaction was completed in a few hours.)

Provenance & Evidence