Acetic Acid → HCID 68576593, compound

Participants

Reaction Steps

Sodium triacetoxyborohydride (4.5 g, 21.23 mmol) is added to a stirred solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.63 g, 13.13 mmol), 2,4-dimethyl-thiazole-5-carboxaldehyde (1.95 g, 13.81 mmol, Maybridge), acetic acid (0.80 ml, 13.98 mmol) and 1,2-dichloroethane (125 ml). The reaction is stirred overnight at room temperature under nitrogen. The reaction is poured into 2N NaOH (300 ml) and extracted with ethyl acetate (200 ml×3). The ethyl acetate is dried over sodium sulfate, filtered, and the filtrate concentrated. The crude product is purified by flash chromatography on silica gel eluting with 0.5% concentrated ammonium hydroxide/5% ethanol/chloroform to yield (2.93 g, 69%) of 4-{[(2,4-dimethyl-thiazol-5-yl)methyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=326.2 (M+1); 1H NMR (CDCl3): δ=4.10 (2H, br m), 3.91 (2H, s), 2.88-2.79 (2H, brm), 2.73-2.66 (1H, m), 2.66 (3H, s), 2.34 (3H, s), 1.86 (2H, brd), 1.48 (9H, s), 1.36-1.24 (3H, m).

Provenance & Evidence