Hydrochloric Acid → 3,4-Piperidinediol, 1-butyl-5-(hydroxymethyl)-, (3R,4R,5R)-

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Reaction Steps

(3R,4R,5R)-3-Benzyloxy-1-(n-butyl)-5-hydroxymethyl-4-piperidinol (105 mg, 0.4 mmol) was dissolved in ethanol (20ml) containing aqueous hydrochloric acid (4N, 0.3 ml), and palladium on carbon (10%, 30mg) was added. The mixture was hydrogenated at 1 atm. H2 -pressure for 3h, filtered through celite and concentrated in vacuo. Purification on a silica gel column (Eluent: ethyl acetate/methanol/25% ammonium hydroxide (4/1/1%)) gave the free base of (3R,4R,5R)-1-butyl-5-hydroxymethyl-3,4-piperidinediol (Yield: 53 mg, 74%) as a semicrystalline compound.

Provenance & Evidence