Sodium Bicarbonate → (R)-3-((R)-(3-chlorophenyl)(4-(methylamino)-4-oxobutoxy)methyl)-N-((S)-1-cyclohexyl-3-(methylamino)propan-2-yl)piperidine-1-carboxamide

Participants

Reaction Steps

tert-butyl (S)-2-((R)-3-((R)-(3-chlorophenyl)(4-(methylamino)-4-oxobutoxy)methyl)piperidine-1-carboxamido)-3-cyclohexylpropyl(methyl)carbamate (50 mg, 0.08 mmol) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (10 mL). The reaction mixture was stirred at rt for 1 h, a solution of saturated sodium bicarbonate was added dropwise to adjust pH=7-8. The resulting mixture was extracted with CH2Cl2 (3×15 mL), washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative HPLC to afford (R)-3-((R)-(3-chlorophenyl)(4-(methylamino)-4-oxobutoxy)methyl)-N—((S)-1-cyclohexyl-3-(methylamino)propan-2-yl)piperidine-1-carboxamide (3.30 mg, yield 8%). 1H NMR (CD3OD, 400 MHz) δ 7.30-7.34 (m, 3H), 7.20 (d, 1H), 4.30 (d, 1H), 4.05 (m, 1H), 3.97 (m, 2H), 2.76 (m, 3H), 2.69 (s, 3H), 2.53 (s, 3H), 2.27 (m, 3H), 1.83 (m, 3H), 1.71 (m, 5H), 1.13-1.28 (m, 10H), 0.89 (m, 4H).

Provenance & Evidence