N-Benzhydryl-1-deoxynojirimycin → Deoxynojirimycin

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A mixture of N-benzhydryl-1-deoxynojirimycin as prepared in Example 2 (Formula VI, 1.00 g, 3.06 mmol) and 20% PD(OH)2 /carbon (0.20 g) in 40 mL of methanol was hydrogenated (60 psig) in a Parr apparatus for 24 h. The mixture was filtered through Celite, and the filtrate was concentrated to a light grey foam. The foam was washed with hexane and then dissolved in water (10 mL) and stirred over Dowex® 50W-X8 ion exchange beads for 2 h. The beads were washed with 1N aqueous NH4OH solution until TLC analysis indicated the product had been completely removed from the resin. The combined ammonia washings were lyophilized to give 0.49 g (99%) of 1-deoxynojirimycin as a white foam, mp 198°-201° C. (literature mp 198°-202° C.: Kinast, G.; Schedel, M. Angew. Chem. Int. Ed. Eng. 1981, 20, 805). The 400-MHz 1H NMR spectrum of the material was identical to that of an authentic sample of 1-deoxynojirimycin (Sigma).

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