Dicyclohexylcarbodiimide → Tert-butyl 3-(3-((1-methylpiperidin-4-yloxy)carbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Participants

Reaction Steps

To a solution of 3-((8-(tert-butoxycarbonyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoic acid (0.15 g, 0.32 mmol), dicyclohexylcarbodiimide (0.079 g, 0.38 mmol) and 4-(dimethylamino)pyridine (0.005 g, 0.038 mmol) in dichloromethane (5 mL), was added (S)-2-butanol (0.037 g, 0.32 mmol). After stirring at room temperature for 60 hours, the reaction mixture was filtered, concentrated in vacuo and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.1 g, 56%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.63-1.66 (m, 4H), 1.89 (br, 2H), 2.15-2.23 (m, 5H), 2.43-2.48 (m, 4H), 3.43 (br, 2H), 3.89 (br, 2H), 4.60-4.65 (m, 4H), 4.95-5.00 (m, 1H), 6.67 (d, 2H, J=8.4 Hz), 6.76 (t, 1H, J=7.6 Hz), 7.17 (t, 2H, J=8.4 Hz), 7.52-7.60 (m, 2H), 7.86-7.91 (m, 2H); MS for C32H42N4O5 m/z 563.06(M+H)+.

Provenance & Evidence