Piperidine → 4-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide

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Reaction Steps

To a 1-L round-bottom flask was added (9H-fluoren-9-yl)methyl (1R)-2-methyl-1-(4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)phenyl)propylcarbamate (10.0 g, 0.0195 mol), ethanol (588 mL), and piperidine (51.7 mL). The solution was stirred at rt for 16 h, then concentrated to give a solid. Flash column chromatography gave 4-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide (2.3 g, 41%). 1H NMR (CDCl3, 400 MHz) δ7.59 (d, J=8.0 Hz, 2H), 7.23 (d, J=8.0 Hz, 2H), 5.00 (m, 1H), 3.95 (m, 1H), 3.59 (m, 2H), 1.83 (m, 4H), 1.57 (m, 3H), 1.20 (m, 1H), J=6.8 Hz, 3H), 0.67 (t, J=6.8 Hz, 3H).

Provenance & Evidence