Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → cis-1-Phenyl-8-(2-phenyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]decan-4-one
Reaktionsgleichung
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C@@H:17]4[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>CO>[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][N:14]([C@H:17]4[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]4[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:13][CH2:12]3)[C:10](=[O:29])[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Komponenten
4
Versuchsvorschrift
Elucidation of absolute stereochemistry: To a solution of 24 mg (cis)-1-phenyl-8-(2-phenyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]decan-4-one (Example 2) in methanol were added 14 mg 1R-(−)-camphorsulfonic acid and the solution stirred for 10 min. at ambient temperature. The resulting salt slurry was evaporated and the residue crystallized from ethyl acetate. With the single crystal X-ray structural analysis of the 1R-(−)-camphorsulfonic acid salt the absolute configuration at the cyclohexane ring was established as 1S and 2S.