CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CO.C(N(CC)CC)C>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:12])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]To a solution of 2-bromomethyl-benzoic acid methyl ester (1.50 g, 6.55 mmol, 1.0 equiv; [CAS RN 2417-73-4]) in methanol (12.5 mL) and triethylamine (1.10 mL) was added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.38 g, 6.88 mmol, 1.05 equiv; commercially available) and the reaction stirred at rt overnight. The reaction mixture was poured on crashed ice, extracted with ethyl acetate, the combined organic phases washed with water and a sat. solution of NaCl, dried over MgSO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (1:1) followed by crystallization from hexane/ethyl acetate to obtain 1.12 g (54%) of the title compound as white crystals. MS (ISP): 261.0 [M-tert-Bu+H]+.
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