Pyrrolidine → 2-[4-((11S,11aS)-7,8-Dimethoxy-11-hydroxy-5-oxo-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyloxymethyl)-phenoxycarbonylamino]-pentanedioic acid

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A solution of the diallyl ester 45 (0.596 g, 0.95 mmol, 1 eq), Pd(PPh3)4 (0.055 g, 0.047 mmol, 0.05 eq) and pyrrolidine (0.34 g, 0.39 mL, 4.7 mmol, 5 eq) in anhydrous CH2Cl2 (18 mL) was stirred at room temperature for 1 h and the solvent removed in vacuo. The residue was washed with EtOAc (3×15 mL), dissolved in MeOH (15 mL) and passed down an IRC 50, weakly acidic, ion exchange column, eluting with MeOH (80 mL). The solvent was removed in vacuo to give the product as a white foam (0.46 g, 88%). 1H NMR (d6 DMSO) δ 7.95 (d, J=6.25 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 7.10 (m, 3H) 6.73 (s, 1H), 5. 49 (d, J=9.2 Hz, 1H), 5.2 (d, J=12.5 Hz, 1H), 4.89 (d, J=12.75 Hz, 1H), 4.00 (m, 1H), 3.80 (m, 7H), 3.45 (m, 4H) 2.30 (t, J=7.5 Hz, 2H), 1.95 (m, 5H). MS (ES+) 602.2.

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