Piperidine → HCID 131713005, compound

Participants

Reaction Conditions

Reaction Steps

3.46 g (15 mmoles) of BOC-Leu-OH are dissolved in 50 ml of ethyl acetate, 2.1 ml (15 mmoles) of triethylamine are added, and the solution is cooled to -15° C. The mixture is stirred at the same temperature, and 1.97 ml (16 mmoles) of pivaloyl chloride are added dropwise, followed by 1.65 ml (16.5 mmoles) of piperidine. The mixture is stirred for 10 minutes between the introduction of the two reactants. When the addition is complete, the mixture is stirred for additional 30 minutes at -10° C., and then it is allowed to stand in a refrigerator overnight. The separated precipitate is filtered off, the filtrate is washed thrice with 10 ml of n hydrochloric acid, each, thrice with 10 ml of n sodium hydrocarbonate solution, each, and then with 10 ml of water, dried over anhydrous sodium sulfate, and evaporated. The oily residue is dissolved in 15 ml of a 4 n solution of hydrochloric acid in ethyl acetate, the mixture is allowed to stand for one hour, then it is diluted with ether and stored in a refrigerator overnight. The precipitate is filtered off to obtain 2.0 g (57%, calculated for BOC-Leu-OH) of H-Leu-piperidine.HCl; m.p.: 123°-125° C., Rf5 =0.45.

Provenance & Evidence