Tetrahydrofurfuryl alcohol → benzyl (3R,4R)-4-amino-3-methoxypiperidine-1-carboxylate

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Reaction Steps

A mixture of 0.123 g (0.42 mmole) of (rac)-(3R,4R)-4-azido-3-methoxy-piperidine-1-carboxylic acid benzyl ester, 0.105 g (0.39 mg-atom) of zinc, 0.20 g of ammonium chloride and 4 mL of tetrahydrofuran-methanol (1:1) was stirred at room temperature for 2 hours and then filtered through a Celite pad, washing with 25 mL of water and 25 mL of tetrahydrofuran. The combined filtrates were made strongly acidic with hydrochloric acid and extracted twice with 25 mL of ethyl acetate. The aqueous layer was made basic with potassium carbonate and extracted three times with 25 mL of ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.069 g of (rac)-(3R,4R)-4-amino-3-methoxy-piperidine-1-carboxylic acid benzyl ester as a colorless oil.

Provenance & Evidence