Compound 13
(±)-tert-butyl 4-(((1R,2S)-2-(4-bromophenyl)cyclopropyl)(tert-butoxycarbonyl)amino)piperidine-1-carboxylate
From: CRISPR-suppressor scanning reveals a nonenzymatic role of LSD1 in AML
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Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To a solution of 12 (170 mg, 0.43 mmol, 1.00 equiv) in CH2Cl2 (4.30 mL) was added Boc2O (281 mg, 1.29 mmol, 3.00 equiv) and 4-dimethylaminopyridine (4-DMAP, 16 mg, 0.13 mmol, 0.30 equiv). The reaction was stirred at room temperature overnight. The mixture was then concentrated under reduced pressure and purified by column chromatography (silica gel, eluent: 0 to 35% EtOAc/hexanes, v/v) to afford carbamate 13 (83%). 1H NMR (500 MHz, DMSO-d6) δ: 7.51–7.30 (m, 2H), 6.99 (d, J = 7.9 Hz, 2H), 4.36–4.00 (m, 2H), 3.87 (s, 1H), 2.72 (s, 2H), 2.57 (s, 1H), 2.25 (ddd, J = 10.1, 6.7, 3.6 Hz, 1H), 1.80 (s, 3H), 1.46 (d, J = 5.6 Hz, 18H), 1.36–1.22 (m, 2H). 13C NMR (126 MHz, DMSO-d6) δ: 154.54, 150.67, 147.65, 138.61, 131.44, 127.93, 120.15, 84.89, 79.73, 58.39, 37.24, 28.37, 27.38, 16.91. HRMS (ESI) (m/z) calc’d for C24H35BrN2O4 [M+H]+: 495.1853, 496.1885, 497.1836, 498.1866, 499.1894 found 495.1846, 496.1883, 497.1826, 498.1862, 499.1895.
