2-(trimethylsilyl)ethyl (2S,3S)-3-((R)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-4-cyclohexyl-2-hydroxybutylcarbamate → (R)-N-((2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-yl)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxy-pentyl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(trimethylsilyl)ethyl (2S,3S)-3-((R)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-4-cyclohexyl-2-hydroxybutylcarbamate (25.8 mg, 0.038 mmol) in acetonitrile (2 mL), tetraethylammonium fluoride (excess) was added. The resulting solution was stirred at 50° C. for 2 h, and purified directly with preparative HPLC to give (R)-N-((2S,3S)-4-amino-1-cyclohexyl-3-hydroxybutan-2-yl)-3-((S)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxy-pentyl)piperidine-1-carboxamide (24.1 mg, 96%) as its TFA salt; 1H NMR (400 MHz, CD3OD) δ 7.54 (dd, 1H), 7.38 (dd, 1H), 7.14 (dd, 1H), 4.36 (d, 1H); 3.94 (m, 2H), 3.78 (m, 1H), 3.28 (m, 2H), 3.24 (s, 3H), 2.94 (dd, 1H), 2.84 (m, 2H), 2.64 (dd, 1H), 2.16 (m, 1H), 1.98 (m, 3H), 0.78-1.86 (m, 20H); MS m/z 542 (M+H+).

Provenance & Evidence