Trifluoroacetic acid → 4-(4-Methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine

Participants

Reaction Conditions

Reaction Steps

Scheme IIA, Step B: To a mixture of 1-(t-butyloxycarbonyl)-4-(4-methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine (1.297 g, 3.77 mmol) in dichloromethane (12 mL) at 0° C. was added trifluoroacetic acid (12 mL). The mixture was stirred at 0° C. for 30 minutes, then at 20° C. for 30 minutes. The mixture was diluted with 2 N sodium hydroxide and extracted 3 times with ethyl acetate. The combined organics were dried over sodium sulfate then filtered and evaporated. The residue was chromatographed over silica gel (dichloromethane/10% methanol/1% ammonium hydroxide in dichloromethane gradient elution) to give the intermediate title compound as a yellow oil (0.738 g, 85%). FDMS m/e=245 (M++1).

Provenance & Evidence