1,2-Dichloroethane → Tert-butyl (2R,5S)-2-[(R)-hydroxy(pyridin-3-yl)methyl]-5-(4-{[5-(1H-pyrazol-1-yl)piperidin-1-yl]carbonyl}benzyl)pyrrolidine-1-carboxylate

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To a solution of 4-{((2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidin-2-yl)methyl}benzoic acid (i-4, 40 mg, 0.1 mmol) and 4-(1H-pyrazol-1-yl)piperidine (15 mg, 0.1 mmol) in 1.0 mL anhydrous DMF was added a 0.5 M solution of HOAt in DMF (0.2 mL, 0.1 mmol) followed by EDC (40 mg, 0.2 mmol) and DIEA (35 μL, 0.2 mmol). The resulting mixture was stirred at RT under nitrogen atmosphere for 16 h. The mixture was washed with water and extracted with dichloromethane (2×5 mL). The organics were combined, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was purified by preparative TLC plate (1000 uM) eluting with 10% MeOH in dichloromethane to afford the title compound (38 mg, 75%). ESI-MS calculated for C31H39N5O4: Exact Mass: 545.30. Found 546.30 (MH)+ and 568.28 (MNa)+.

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