[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([C:16]#[C:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](/[CH:16]=[CH:17]\[CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Add 3-(tert-butoxycarbonylamino-methyl)-6-cyclohexylethynyl-pyridine (0.7 g, 2.21 mmol) and Lindlar's Catalyst (0.1 g) to EtOAc (20 mL). Bubble hydrogen (via balloon) through the mixture for 2 h and stir under static atmosphere of hydrogen overnight. Filter the catalyst through Celite® and concentrate the filtrate in vacuo. Purify the crude mixture by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 9:1 gradient over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (0.21 g, 30%) and starting material (0.42 g, 60%). Repeat the reaction on the recovered starting material to obtain the desired intermediate (242 mg, 57%; 452 mg total, 64% overall). MS (APCI+) m/z: 217 (M-Boc+H)+.
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