[CH3:1]OC(C1C(N)N(CC2C=CC=CC=2)CCC=1)=O.[OH-].[Na+].[CH3:21][O:22][C:23]([C:25]1[CH2:26][N:27]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28][CH2:29][C:30]=1[NH2:31])=[O:24].C(O)(C(F)(F)F)=O.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C.C1COCC1>[CH2:21]([O:22][C:23]([CH:25]1[CH:30]([NH2:31])[CH2:29][CH2:28][N:27]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:26]1)=[O:24])[CH3:1]
Amino-1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester BH3 salt was heated in ethanol with NaOH 25%. After 72 h at 50° C. the mixture was cooled, washed with water/ice and extracted with AcOEt. The extract was washed with brine and dried over sodium sulfate. Removal of the solvent under reduced pressure gave an yellow oil. To a suspension of 4-amino-1-benzyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (21 g) in 200 ml THF was added 50 ml TFA at 10° C. under an argon atmosphere. After stirring for 15 min at 0° C., NaBH4 (6.43 g) was added over a period of 75 min at 10° C. The mixture was stirred for additional 90 min at 0° C. After adding 100 ml NH4Cl saturated, the solution was extracted two times with CH2Cl2. The combined extracts were washed with water/ice and brine and dried over sodium sulfate. Evaporation of the solvent gave a yellow oil of the title compound which was taken for the next step without purification
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