Ethanol → (1R*,2R*)-2-[5-(4-Chloro-phenyl)-3-methyl-3H-[1,3,4]thiadiazol-2-ylideneamino]-cyclohexanol

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Reaction Steps

The compound I8 was prepared by the procedure described in Example I3 using appropriate intermediates and reagents (Protocol A). Triethylamine was replaced by morpholine resin (2.1 mmol, 0.61 g, loading 3.47 mmol/g); the mixture of morpholine resin and trans-2-aminocyclohexanol hydrochloride (2.1 mmol, 0.318 g) was stirred in ethanol (3.5 mL) at RT for 5 minutes before the addition of 3-methyl-2-methylthio[1,3,4]thiadiazolium perchlorate (3a) (0.7 mmol, 0.25 g). The residue was subjected to silica gel chromatography (Alltech column, 2 g silica) eluting with dichloromethane containing from 0% to 1% methanol. Yield: 0.050 g, 22%.

Provenance & Evidence