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

HRID 620910Notes

Reaction equation

HRID 620910 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

HCID 128066742,2-Dimethyl-8-phenoxy-4-(1H-1,2,4-triazol-1-yl)octan-3-one

Product 1

HCID 12806676(3-R*,4-S*)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-8-phenoxy-octan-3-olYield 97.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. customat 125°
  2. filtrationThe hydrogenation catalyst was filtered off
  3. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-2d3151ec23cd4f2a9057c165771c5564
Source dataset
uspto-grants-1989_04
Patent number
US04822889

Reaction notes

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