[S:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C1(=O)[N:11](NCCCBr)[C:10](=O)[C:9]2=CC=CC=[C:8]12.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[BH4-].[Na+]>C(#N)C.C(O)(=O)C.O.C(O)(C)C>[NH2:11][CH2:10][CH2:9][CH2:8][N:3]1[CH2:4][CH2:5][S:1][C:2]1=[O:6]
To a solution of 2-thiazolidinone (0.994 g, 9.64 mmol) in acetonitrile (10 ml) were added N-phthalimido-3-bromopropylamine (2.88 g, 10.7 mmol), potassium carbonate (1.64 g, 11.9 mmol), and 18-crown-6 (catalytic amount). The mixture was refluxed about 17 hours, solvent was removed in vacuo, and the resulting solid was redissolved in 1 M potassium chloride and dichloromethane (˜25 ml each). The aqueous phase was separated and extracted with 2×25 ml dichloromethane. The combined organic fraction was dried over sodium sulfate, filtered, and dried in vacuo. The crude product was recrystallized from acetone/methanol to give 1.54 g (55% yield). To a warmed solution of the phthalimido protected amine (1.53 g, 5.27 mmol) in 6:1 isopropanol:water was added sodium borohydride (1.01 g, 26.7 mmol), and the mixture was stirred at 60° C. for 22 hours. Glacial acetic acid (5.4 ml) was added, and the solution was stirred at 80° C. for 2 hours, then the solution was cooled and dried in vacuo. The product was redissolved in 6 N hydrochloric acid, washed with ether (2×30 ml), then dried in vacuo. The product was purified via recrystallization from hot water.
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