Hydrochloric Acid → 6-Amino-alpha-[[(1 methylcyclopentyl)amino]methyl]-3-pyridinemethanol dihydrochloride

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Reaction Steps

To a solution of 349 mg of (R)-α-[[(1-methyl cyclopentyl)amino]methyl]tetrazolo[1,5-a]pyridine-6-methanol and 0.11 ml of 12 N HCl in 28 ml of methanol, 609 mg of SnCl2 108 2H2O was added and the resulting mixture heated at reflux with stirring for 16 hours. The reaction mixture was concentrated to dryness and the residue partitioned between 25 ml of 80:20 methylene chloride:methanol and 5 ml of 2.5 N NaOH solution. The layers were vigorously stirred and then separated. The aqueous layer was repeatedly extracted with methylene chloride/methanol. The combined extracts were dried with anhydrous magnesium sulfate and concentrated to give 473 mg of crude product. Purification was affected on silica gel prep Tlc plates (80:20:1 methylene chloride: methanol:NH4OH) to give 153 mg of product. Treatment with ethanolic HCl solution followed by precipitation with ether afforded the hydrochloride salt, 140 mq. Analysis: Calc'd. for C13H21N3O·2HCl:

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