2,6-Di-tert-butylpyridine → Ethyl 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoate

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Reaction Steps

To a solution of ethyl 3-(bromomethyl)-5-(1-cyanocyclopentyl)benzoate (0.15 g, 0.45 mmol) and 2-tert-butoxycarbonylamino-2-methyl-3-phenylpropan-1-ol (0.21 g, 0.79 mmol in 8 mL dichloroethane was added 2,6-di-tert-butylpyridine, polymer bound (0.72 g, 1.3 mmol) and silver trifluoromethanesulfonate (0.20 g, 0.79 mmol). The reaction was stirred at rt overnight and filtered. Concentration and flash chromatography (silica gel, 0-25% EtOAc/hexanes) gave ethyl 3-((2-tert-butoxycarbonylamino-2-methyl-3-phenylpropoxy)methyl)-5-(1-cyanocyclopentyl)benzoate. 1H NMR (400 MHz, CDCl3) δ 8.03 (app d, J=1.5 Hz, 1H), 7.96 (s, 1H), 7.67 (s, 1H), 7.28-7.22 (m, 3H), 7.17 (m, 2H), 4.60 (s, 2H), 4.57 (s, 1H), 4.40 (q, J=7.1 Hz, 2H), 3.55 (d, J=8.9 Hz, 1H), 3.45 (d, J=9.0 Hz, 1H), 3.14 (d, J=13.3 Hz, 1H), 2.95 (d, J=13.2 Hz, 1H), 2.52 (m, 2H), 2.13-1.96 (m, 6H), 1.46 (s, 9H), 1.41 (t, J=7.1 Hz, 3H), 1.28 (s, 3H).

Provenance & Evidence