Bicyclic 1,3-aminoalcohols, d8-metal complexes and hydrogenation processes

Process for the preparation of compounds of formula I in the form of their racemates, mixtures of diastereoisomers or substantially pure diastereoisomers,

• wherein
• W signifies a direct bond or C1-C4-alkylene, X is a direct bond or C1-C4-alkylene, Y is C1-C4-alkylene,
• R1 signifies hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C10-aryl, or C7-C12-aralkyl,
• R2 is hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C6-C10-aryl, or C7-C12-aralkyl, C1-C8-carboxylic acyl, C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, (R6)2P(O)—, or R6SO2—,
• R3 signifies C1-C6-alkyl, cyclohexyl, phenyl or benzyl,
• R4 and R5, independently of one another, are C1-C6-alkyl, cyclohexyl, phenyl or benzyl, and
• R6 is C1-C6-alkyl, C1-C6-halogenalkyl;
• or cyclohexyl, phenyl or benzyl either unsubstituted or substituted by C1-C4-alkyl, C1-C4-halogenalkyl, or C1-C4-alkoxy;
• whereby aliphatic, saturated or ethylenically unsaturated and/or aromatic hydrocarbon rings are optionally condensed onto the rings of the bicyclic ring system, and
• the optionally condensed bicyclic ring system is unsubstituted or is substituted by C1-C6-alkyl, C1-C6-alkoxy, cyclohexyl, C6-C10-aryl, C7-C12-aralkyl, C1-C4-alkyl-C6-C10-aryl, C1-C4-alkoxy-C6C10-aryl, C1-C4-alkyl-C7-C12-aralkyl, C1-C4-alkoxy-C7-C12-aralkyl;
• as well as the acid addition salts thereof, in which process
• a) a compound of formula II
• wherein W, X and Y are defined as indicated above, is reacted with a phosphoric acid ester azide in the presence of an alcohol R—OH, wherein R signifies C1-C6-alkyl, C5-C8-cycloalkyl, C5-C8-cycloalkyl-C1-C4-alkyl, benzyl, or benzyl substituted by C1-C4-alkyl, to form a compound of formula III,
• b) the compound of formula III is cyclised with bromine, iodine or an electrophilic brominating or iodising agent to form a compound of formula IV, wherein X′ is Br or I,
• c) in the compound of formula IV, the halogen is substituted by hydrogen to form a compound of formula V,
• d) the compound of formula V is hydrolysed or reduced to the compound of formula VI,
• e) or in the compound of formula V, the hydrogen atom of the NH group is substituted by the group R′2 to form compounds of formula VII, wherein R′2 signifies C1-C6-alkyl, C3-C8-cycloalkyl, C6-C10-aryl, or C7-C12-aralkyl, and then the compounds of formula VII are hydrolysed or reduced to compounds of formula VIII,
• f) or the compounds of formula VI are reacted with C1-C6-alkoxycarbonates, C1-C6-alkylamino- or C1-C6-dialkylamino-carbonyl halides, C1-C8-carboxylic acid halides, C1-C6-alkoxy-carbonyl halides, (R6)2P(O)-halides or R6—SO2-esters or halides, to form compounds of formula IX, wherein R″2 signifies C1-C6-alkoxycarbonyl, C1-C8-carboxylic acyl, C1-C6-alkylamino-, C1-C6-dialkylaminocarbonyl or the groups (R6)2P(O)— and R6—SO2—,
• g) and in compounds of formulae VI, VIII and IX, the OH group is etherified to compounds of formula X, R1 signifies C1-C6-alkyl, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C10-aryl, or C7-C12-aralkyl, and R2 is defined as indicated for formula I,