2,2-Dimethyl-8-phenoxy-4-(1H-1,2,4-triazol-1-yl)octan-3-one → (3-R*,4-S*)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-8-phenoxy-octan-3-ol
Reaction equation
[CH3:1][C:2]([CH3:23])([C:4](=[O:22])[CH:5]([N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:3]>O1CCOCC1>[CH3:3][C:2]([CH3:23])([C@@H:4]([OH:22])[C@@H:5]([N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:1]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
280 g of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-8-phenoxyoctan-3-one were dissolved in 1.8 liters of dioxane, 10 g of RuO(OH)x were added, and hydrogenation was then carried out in an autoclave for 62 hours under a hydrogen pressure of 25 bar and at 125°. The hydrogenation catalyst was filtered off and the solvent distilled off to give 274 g of residue; according to NMR analysis, this residue contained, in addition to 5% of the starting ketone, the compound No. 1 (R*,S*) and its diastereomer (R*,R*) in a ratio of 7:3. It was possible to isolate the compound No. 1 from the mixture by crystallization from diisopropyl ether.