反应详情

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)+.

1. filtrationFilter the catalyst through Celite®
2. concentrationconcentrate the filtrate in vacuo
3. customPurify the crude mixture by chromatography on silica gel (80 g, pre-packed cartridge)
4. washeluting with hexane/EtOAc (1:0 to 9:1 gradient over 1.25 h, 80 mL/min)