反应详情

(1R,2S,3R,4R)-2,3-Dihydroxy-4-(hydroxylmethyl)-1-aminocyclopentan hydro-chloride (70.0 g, 380 mmol) was dissolved in water (660 ml) and FmocOSU (N-(9-Fluorenylmethoxycarbonyloxy)-succinimid) (148.5 g, 440 mmol) solved in dioxan (2.00 l) was added. Then saturated sodium hydrogencarbonate solution (800 ml, 880 mmol) was added slowly. The mixture was stirred 3 h at room temperature until TLC (Silicagel Merck 60, chloroform/methanol/acetic acid 8:2+0.1% v/v/v) showed complete consumption of the educts. The obtained precipitate was filtered off and the filtrate was added to water (6.00 l). The resulting suspension was stirred for 5 min and then stored 12 h at 4° C. The resulting suspension was filtered. The obtained solid was washed with cold water (3.00 l) and dried 12 h under reduced pressure at 45° C. over calcium chloride. For a further purification the crude product was suspended in ethylacetate, stirred 1 h, filtered and dried under reduced pressure yielding 134 g (95%) of the title compound as white solid.

1. additionwas added
2. customconsumption of the educts
3. filtrationThe obtained precipitate was filtered off
4. additionthe filtrate was added to water (6.00 l)
5. waitstored 12 h at 4° C
6. filtrationThe resulting suspension was filtered
7. washThe obtained solid was washed with cold water (3.00 l)
8. dry with materialdried 12 h under reduced pressure at 45° C. over calcium chloride
9. customFor a further purification the crude product
10. stirringstirred 1 h
11. filtrationfiltered
12. customdried under reduced pressure