Reaction SMILES: BrC(C)(C)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:10](C#N)[C:11]1[CH:16]=[CH:15]C=C[CH:12]=1.COC1C=C(C=CC=1)CC#[N:26].BrC(CC(C)C)(CC)C(OCC)=O.Cl[Si](C)(C)C>ClCCl.O1CCCC1.[Zn]>[NH2:26][CH:16]([CH3:15])[C:11]([CH3:10])([CH3:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4]
Reactant: CCOC(=O)C(C)(C)Br
Reactant: COc1cccc(CC#N)c1
Reactant: N#CCc1ccccc1
Agent: CCOC(=O)C(Br)(CC)CC(C)C
Agent: C[Si](C)(C)Cl
Agent: [Zn]
Solvent: ClCCl
Solvent: C1CCOC1
Product: CCOC(=O)C(C)(C)C(C)N

Procedure:
Process for preparing norbenzomorphan of general formula 1 wherein R1 is defined as in claim 1, according to claim 3, characterised in that a) a benzylcyanide of general formula 2 is reacted with ethyl bromoisobutylbutyrate (3) in the presence of chlorotrimethylsilane and zinc powder in dichloromethane after diluting with tetrahydrofuran, the reaction mixture is heated, then when the reaction has ended it is allowed to cool, the zinc powder is separated off and the reaction mixture is combined with sodium cyanoborohydride and the resulting mixture is diluted with ethanol and then mixed with concentrated aqueous ammonia solution, the organic phase is separated off and evaporated down, the residue is taken up in toluene, the solution obtained is extracted with 2 N hydrochloric acid, the combined aqueous extracts are made alkaline with concentrated aqueous ammonia solution, this alkaline solution is extracted with dichloromethane and the resulting ethyl 3-amino-2,2-dimethylbutanoate derivative of general formula 4 is isolated ##STR44## and b) the ethyl 3-amino-2,2-dimethylbutanoate derivative of general formula 4 is subjected to a Michael addition reaction with ethyl acrylate in ethanol as solvent, the reaction medium is removed once the reaction has ended and the resulting ethyl 3-(2-ethoxycarbonylethyl)amino-2,2-dimethylbutanoate derivative of general formula 5 is isolated ##STR45## and c) the ethyl 3-(2-ethoxycarbonylethyl)amino-2,2-dimethylbutanoate derivative of general formula 5 thus obtained is subjected to the conditions of a Dieckmann ester condensation in toluene in the presence of potassium tert.-butoxide, the volatile components of the reaction mixture resulting from the reaction of cyclisation are eliminated by distillation, then the mixture is hydrolysed and combined with concentrated hydrochloric acid, the resulting mixture is combined with diethylether and concentrated ammonia solution, the combined organic extracts are evaporated down and the resulting piperidone derivative of general formula 6 is isolated ##STR46## and d) the piperidone derivative 6 is saponified in an ethanol/water mixture in the presence of sodium hydroxide or hydrochloric acid or sulphuric acid, whilst heating to reflux temperature, and decarboxylated to obtain the corresponding 3,3-dimethylpiperidone derivative of general formula 7, the reaction product is isolated and the corresponding hydrohalide is optionally prepared with hydrochloric or hydrobromic acid ##STR47## and e) the mixture of stereoisomers thus obtained is dissolved in ethanol, optionally after liberation of the enantiomeric free bases, mixed with the corresponding enantiomer (D- or L-form) of tartaric acid, the desired stereoisomer is isolated in the form of the corresponding tartrate, the mother liquor containing the unwanted isomer is heated and in this way the unwanted enantiomer is converted thermally into the desired stereoisomer, then mixed with D- or L-tartaric acid and the desired stereoisomer thus present as the corresponding tartrate is optionally crystallised by the addition of isopropanol and the precipitate is isolated and this procedure is repeated as necessary ##STR48## and f) the pure stereoisomer thus obtained, after liberation from the enantiomerically pure acid addition salt, is subjected to a Wittig reaction in tetrahydrofuran with methyl triphenylphosphonium bromide in the presence of potassium tert.-butoxide at a temperature of 40° C., then when the reaction has ended the mixture is combined with water and dichloromethane, the aqueous phase is extracted exhaustively, the reaction product of type 9 or the corresponding stereoisomer is isolated in the form of its hydrohalide ##STR49## and g) the alkene 9 obtained from the Wittig reaction is optionally first liberated from its acid addition salt and the free base of type 9 is dissolved in toluene and subjected with n-butylformate to a reaction of formylation at the piperidine nitrogen and the reaction product of type 10 or the corresponding stereoisomer thereof is isolated ##STR50## and h) the formyl compound 10--or the corresponding stereoisomer--thus obtained is dissolved in dichloromethane and reacted with aluminium(III)chloride at a temperature of not more than -5° C. and the cyclisation product of type 11 resulting from this reaction is isolated ##STR51## and i) the benzomorphan derivative 11 resulting from the reaction of cyclisation is dissolved in n-propanol and reacted with concentrated hydrochloric acid and the deformylated norbenzomorphan of type 12 resulting from this reaction is isolated in the form of its hydrochloride ##STR52## and j) if desired, after liberation of the free benzomorphan base, the substituent R2, if it denotes an alkoxy group, is converted by ether splitting into a free hydroxy function and the reaction product is isolated, optionally after the addition of hydrochloric or hydrobromic acid, in the form of its hydrohalide of general formula 13, the base corresponding to general formula 1. ##STR53##