Diisopropylethylamine → 1-((1R,5S)-8-{2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole

Participants

Reaction Steps

To a solution of [3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]acetaldehyde (50.4 mg, 0.17 mmol), 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-3-yl]-2-methyl-1H-benzimidazole dihydrochloride (64 mg, 0.17 mmol) and diisopropylethylamine (0.063 mL, 0.35 mmol) in 2 mL CH2Cl2 was added sodium triacetoxyborohydride (55 mg, 0.26 mmol) and the reaction mixture was stirred for 2 h at room temperature. After evaporation, the residue was chromatographed (5% (2M NH3/MeOH) in CHCl3) to provide 1-((1R,5S)-8-{2-[3-(2,2-dimethylpropanoyl)-6-phenyl-1,3-oxazinan-6-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole (50.4 mg, 56%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.65 (m, 1H), 7.43-7.34 (m, 4H), 7.32-7.26 (m, 2H), 7.19-7.11 (m, 2H), 5.43 (s, 1H, J=11.2 Hz), 4.70 (d, 1H, J=10.3 Hz), 4.61 (m, 1H), 4.21 (m, 1H), 3.42-3.22 (m, 2H), 3.08 (m, 1H), 2.57 (s, 3H), 2.43-1.57 (m, 14H), 1.28 (s, 9H); ESI-MS 515 (M+H), 237 (M+Na).

Provenance & Evidence