[CH2:1]([O:4][CH:5]([CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15](COCC[Si](C)(C)C)[CH:14]=[CH:13]2)[C:6]([OH:8])=[O:7])[CH2:2][CH3:3].C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([CH2:9][CH:5]([O:4][CH2:1][CH2:2][CH3:3])[C:6]([OH:8])=[O:7])=[CH:18][CH:17]=2)[CH:13]=[CH:14]10.96 g rac-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid were dissolved in 40 ml N,N-dimethylformamide. 0.94 ml Ethylene diamine were added, followed by 7.63 ml of a tetra-butylammonium fluoride solution (1 molar in tetrahydrofuran); a small amount of molecular sieves was then added to the reaction mixture and it was heated to 80° C. After 6 hours, the mixture was cooled to r.t., filtered and the filtrate was poured into ice water and extracted 3 times with dichloromethane. The organic phases were washed with water, dried over MgSO4, filtered again and evaporated. The crude rac-3-(1H-indol-5-yl)-2-propoxy-propionic acid was used for the next step without purification.
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