[CH2:1]([N:3]1[CH2:7][C@@H:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:5]([OH:17])[CH2:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[K+]>C(Cl)Cl.C(O)C.O>[CH2:1]([N:3]1[CH2:4][C@@H:5]([OH:17])[C@H:6]([N:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:7]1)[CH3:2]
To a stirring slurry of 3.5 g (0.15 mole) of trans-1-ethyl-4-[(2-phenylethyl)amino]-3-pyrrolidinol and 5 g potassium carbonate in 75 ml of methylene chloride at ice bath temperature was added dropwise a solution of 3.2 g (0.023 mole) of benzoyl chloride in 25 ml of methylene chloride. After addition was complete, the mixture was stirred at ambient temperature overnight. The mixture was filtered through Celite and the filtrate was concentrated to give a yellow gum as residue. An NMR analysis of this gum indicated that it was a mixture of desired amide and the di-substituted amide-ester. The gum was dissolved in 50 ml ethanol and a solution of 0.5 g (0.08 mole) potassium hydroxide in 10 ml of water was added. The mixture was heated at reflux for 3 hr. The solution was concentrated and water was added to the residue. The mixture was extracted with methylene chloride and the combined extracts were dried over anhydrous sodium sulfate and concentrated to give 4.9 g (98%) of gum as residue. The gum crystallized upon standing and the solid was recrystallized from cyclohexane to yield white solid, m.p. 71°-75° C.
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