Hydrochloric Acid → HCID 15485234, compound

Participants

Reaction Steps

A solution of 2.2 g (5 mmol) (S)-{1-benzyl-2-[4-hydroxy-4-(3-methoxy-thiophen-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester in 20 mL tetrahydrofuran was treated at once with 20 mL 3M hydrochloric acid. The reaction mixture was stirred at ambient temperature overnight and then extracted with 50 mL diethyl ether. The remaining aqueous layer was basefied with sodium bicarbonate powder and extracted with chloroform (3×60 mL). The combined organic extract was dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was flash chromatographed on 60 g silica gel. Elution with 2% methanol in chloroform yielded both, 100 mg of the title compound as a yellowish oil and 700 mg of (1S)-1-benzyl-2-[4-(3-methoxy-thiophen-2-yl)-3,6-dihydro-2H-pyridin-1-yl]-ethylamine as an amber oil.

Provenance & Evidence