F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][O:35][C@@H:34]([C:38]([OH:40])=O)[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C.N1CCCC1>ClCCl>[N:13]1([C:38]([C@@H:34]2[O:35][CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[CH2:33]2)=[O:40])[CH2:14][CH2:15][CH2:16][CH2:11]1O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluronium hexafluorophosphate (HATU) (1.47 g, 4.3 mmol) was added to a solution of (R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (1 g, 4.3 mmol) and diisopropylethylamine (1.11 g, 8.6 mmol) in anhydrous dichloromethane (20 mL) at room temperature. Pyrrolidine (0.45 mL, 5.62 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The mixture was partitioned between water and dichloromethane. The organics were dried over sodium sulfate and concentrated under reduced pressure and the resulting residue was purified via column chromatography (100-200 mesh silica gel, 0-0.5% methanol in dichloromethane) to afford (R)-tert-butyl 2-(pyrrolidine-1-carbonyl)morpholine-4-carboxylate (0.62 g).
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