Sodium Iodide → N-(tert-butoxycarbonyl)piperidine

Participants

Reaction Steps

To a solution of 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester (537 mg, 2.1 mmol, 1 eq.) and 4-chloromethyl-thiazole (280 mg, 2.10 mmol, 1 eq.) in anhydrous dimethylformamide (6 mL) is added sodium iodide (66 mg, 0.44 mmol, 0.2 eq.) and potassium carbonate (354 mg, 2.5 mmol, 1.2 eq.), the reaction mixture is stirred at room temperature for 3 days, and then water and ethyl acetate are added. The layers are separated, and the aqueous layer is extracted with ethyl acetate. The combined organics are dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude material is purified using medium pressure liquid chromatography eluting from 0 to 25% THF in hexanes to afford 4-}isobutyl-[(thiazol-4-yl)methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (559 mg, 75%). m/z=354 (M+1); 1H NMR (CDCl3): δ=8.68 (1H, brs), 7.16 (1H, brs), 4.11 (2H, brs), 3.80 (2H, brs), 2.58 (3H, brs), 2.25-2.22 (2H, m), 1.71-1.57 (3H, m), 1.46-1.32 (11H, m), 0.82 (6H, d).

Provenance & Evidence