Sodium triacetoxyborohydride → 2-methyl-1-{[1-methyl-4-(1H-1,2,4-triazol-3-ylamino)cyclohexyl]oxy}propan-2-ol

HRID 1412481Notes

Reaction equation

HRID 1412481 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[OH:7][C:8]([CH3:20])([CH3:19])[CH2:9][O:10][C:11]1([CH3:18])[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(=O)([O-])O.[Na+]>[CH3:20][C:8]([OH:7])([CH3:19])[CH2:9][O:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([NH:1][C:2]2[N:6]=[CH:5][NH:4][N:3]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 670098904-(2-Hydroxy-2-methylpropoxy)-4-methylcyclohexanoneHCID 178418311HCID 178418311, compound

Product 1

HCID 1784593832-methyl-1-{[1-methyl-4-(1H-1,2,4-triazol-3-ylamino)cyclohexyl]oxy}propan-2-olYield 57.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-amino-1H-1,2,4-triazole (441 mg) and 4-(2-hydroxy-2-methylpropoxy)-4-methylcyclohexanone (1.05 g) in acetic acid (10 mL) was added sodium triacetoxyborohydride (1.67 g), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate-isopropyl alcohol (3:1). The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→10/90 (volume ratio)] to give colorless amorphous 2-methyl-1-{[1-methyl-4-(1H-1,2,4-triazol-3-ylamino)cyclohexyl]oxy}propan-2-ol (810 mg, 54%) as a diastereomixture.

Workup

  1. extractionthe mixture was extracted with ethyl acetate-isopropyl alcohol (3:1)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→10/90 (volume ratio)]

Sources & evidence

ORD record
ord-1424bd101f1040c08358982276656cbc
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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