Water → HCID 86627793, compound

Participants

Reaction Steps

To a solution of the crude 4-[2-(6-chloro-2-methanesulfonylpyrimidin-4-yl oxy)ethyl]-piperidine-1-carboxylic acid tert-butyl ester (4.9 g) and NaCN (14 mmol) in CH2Cl2:H2O (50 mL, 4:1) is added TBAB (tetrabutylammonium bromide) (0.06 mmol) at room temperature. After stirring at the same temperature for 10 h, TBAB (0.19 mml) is added to the reaction mixture. The reaction mixture is stirred at room temperature for 2 h and H2O is added. The organic layer is separated, dried over MgSO4 and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give 4-[2-(6-chloro-2-cyanopyrimidin-4-yloxy)ethyl]piperidine-1-carboxylic acid tert-butyl ester; 1H-NMR (CDCl3), δ: 1.14-1.28 (2H, m), 1.45 (9H, s), 1.56-1.78 (7H, m), 2.69 (2H, t), 4.11 (2H, m), 4.49 (2H, t), 6.93 (1H, s).

Provenance & Evidence