1H-1,2,4-Triazole → HCID 19835579, compound

HRID 477398Notes

Reaction equation

[C:1]([C:5]1([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1>CN(C)C=O>[C:1]([C:5]([OH:6])([CH2:7][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 160 g (0.75 mol) of 2-tert.-butyl-2-(tetrahydro-2H-pyran-2-yloxymethyl)-oxirane in 180 ml of absolute dimethylformamide is added dropwise to a mixture of 168 g (2.45 mols) of 1,2,4-triazole, 18.2 g (0.16 mol) of potassium tert.-butylate and 350 ml of absolute dimethylformamide at 80° C. under a nitrogen atmosphere. The reaction mixture is stirred at 80° C. for 6 hours and is then concentrated by stripping off the diluent under reduced pressure. The residue which remains is taken up in ethyl acetate and the organic solution formed is washed with water and then dried over sodium sulphate, and concentrated by stripping off the solvent under reduced pressure. The product thus obtained is purified chromatographically over silica gel with chloroform as the mobile phase. 107.3 g (51% of theory) of 2-tert.-butyl-1-(tetrahydro-2H-pyran-2-yl-oxy)-3-(1,2,4-triazol-1-yl)-propan-2-ol (mixture of diastereomers) are obtained in this manner.

Workup

concentrationis then concentrated
customthe organic solution formed
washis washed with water
dry with materialdried over sodium sulphate
concentrationconcentrated
customThe product thus obtained
customis purified chromatographically over silica gel with chloroform as the mobile phase

Sources & evidence

ORD record: ord-9416561e83ff4373a0fdffbf5238ab4c
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04888048

Reaction notes

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