Trifluoroacetic acid → 2-Phenyl-2-o-tolylethanamine

Participants

Reaction Steps

Potassium tert-butoxyde (8.64 g, 77 mmol) was added, in one portion, to a cold (0° C.) solution of Tosmic (6.04 g, 27.8 mmol) in DMSO (15 mL) and stirred for 5 min. MeOH (0.2 mL) was then added followed by phenyl(o-tolyl)methanone (1.82 g, 9.2 mmol) in one portion. The reaction was warmed up slowly over 12 hours to room temperature. The reaction mixture was partitioned between saturated aqueous sodium carbonate and ethyl acetate. The organic phase was dried over sodium sulfate and evaporated under reduced pressure to give a residue. TFA (3.85 mL, 50 mmol) in THF (5 mL) was slowly added to a cool (0° C.) suspension of sodium borohydride (2.1 g, 50 mmol) in THF (5 mL) over 10 minutes. To this solution was added the residue dissolved in THF (5 mL) over 5 minutes. The resulting mixture was warmed to room temperature and stirred 16 hrs. The reaction mixture was partitioned between saturated aqueous sodium carbonate and ethyl acetate. The organic phase was dried over sodium sulfate and evaporated under reduced pressure and dissolved in methanol. This solution was then passed through SCX resin (12 g, 0.78 mmol/g) and washed with methanol. These washes were discarded and the cartridge treated with 2M ammonia in methanol. The ammonia solution was then evaporated to generate the desired compound (1.322 g, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm: 2.22 (3H, s) 3.04-3.16 (2H, m) 4.13 (1H, t, J=7.45 Hz) 7.08-7.31 (11H, m).

Provenance & Evidence