1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 86609476, compound

Participants

Reaction Steps

To a solution of (E)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidin-4-ol (3.67 g) in N,N-dimethylformamide (50 ml) were added thioacetic acid (4.6 ml) and N,N-dimethylformamide dineopentylacetal (18 ml). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride successively, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (1:9 to 1:1) as the eluent to afford crude (E)-4-(acetylsulfanyl)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidine (4.29 g) as a brown oil. To a solution of the above oil in dichloromethane (50 ml) was added trifluoroacetic acid (1.5 ml) at 0° C. The resulting mixture was stirred at room temperature for 30 minutes, and the solvent was removed in vacuo. The residue was purified twice by chromatography on silica gel using a mixture of methanol and dichloromethane (1:99 to 7:93) as the eluent to afford the title compound as a brown oil (1.46 g, overall yield: 37%).

Provenance & Evidence