[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9](O[Cl:14])(C)(C)C.C(O)C.C1CCCC=CC=1>C(Cl)Cl.C(OCC)C.C(O)(C)C>[ClH:14].[CH:1]12[CH:9]=[CH:2][CH:3]([O:8][NH:7]1)[CH2:4][CH2:5][CH2:6]2
To a solution of 16.8 g (0.149 mol) cyclohexanone oxime in 240 ml methylene chloride was slowly added at 0° C. 19.4 g (0.178 mol) tert.-butyl-hypochlorite. The resulting dark blue solution was cooled to −20° C. and then 30 ml ethanol and 20.0 g (0.212 mol) 1,3-cycloheptadiene were added and the mixture was stored in a freezer at 5° C. for 2 days until the blue color had disappeared. The reaction mixture was added to 30 ml isopropanol and then 300 ml diethyl ether and after stirring for 3 h the resulting precipitate was isolated by suction to yield 18.6 g of 6-oxa-7-aza-bicyclo[3.2.2]non-8-ene hydrochloride. 9.0 g (0.072 mol) of this material were hydrogenated with palladium on activated carbon at 5 bar hydrogen. After complete conversion the catalyst was filtered off and a solution of 30 ml 4 M hydrochloric acid in dioxane was added. After evaporation the residue was crystallized from 20 ml isopropanol and 500 ml diethyl ether giving 7.5 g cis-4-amino-cycloheptanol as hydrochloride.
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