Acetic Acid → HCID 86607900, compound

Participants

Reaction Steps

To 324 mg (0.599 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) was added methanol (5 mL), acetic acid (300 μL), acetone (135 μL), and sodium cyanoborohydride (61 mg, 0.971 mmol) and the resulting reaction was stirred at room temperature overnight. The reaction mixture was then concentrated and the residue was taken up in saturated aqueous sodium carbonate and extracted with ethyl acetate (3×). the combined organic extracts were dried over Na2SO4 and purified using column chromatography on silica gel eluting with 1% methanol/CH2Cl2 to give (3S,4R)-N-tert-butoxy-1-isopropyl-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (205 mg, 0.352 mmol, 59%) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.91 (s, 3H) 1.05 (dd, J=6.57, 1.26 Hz, 5H) 1.23-1.26 (m, 8H) 1.55-1.64 (m, 4H) 1.95 (dd, J=13.64, 4.04 Hz, 1H) 2.09 (d, J=12.38 Hz, 1H) 2.27 (td, J=12.13, 3.03 Hz, 1H) 2.73-2.81 (m, 4H) 2.85 (d, J=4.29 Hz, 1H) 2.91-3.01 (m, 2H) 5.57 (d, J=1.01 Hz, 2H) 6.01 (d, J=7.33 Hz, 1H) 7.09 (ddd, J=9.41, 2.78, 2.46 Hz, 2H) 7.42 (s, 1H) 7.56 (ddd, J=8.34, 7.07, 1.26 Hz, 1H) 7.74 (ddd, J=8.46, 6.95, 1.26 Hz, 1H) 7.83-7.87 (m, 2H) 7.89-7.94 (m, 1H) 8.09 (d, J=7.83 Hz, 1H).

Provenance & Evidence