Cyclohexanecarboxylic acid, 3-hydroxy-, methyl ester, (1S,3R)- → HCID 23658346, compound

Participants

Reaction Steps

Methyl (1S)-3-(4,5-diphenylpyrimidin-2-yloxy)cyclohexanecarboxylate 1.5 g (2.12 mmol) of diphenylperfluorodecylphosphine were added to a solution of 280 mg (1.76 mmol) of methyl (1S,3R)-3-hydroxycyclohexanecarboxylate in 2 ml of tetrahydrofuran. After 30 minutes, 525 mg (2.12 mmol) of 4,5-diphenylpyrimidin-2-ol and 2 ml of tetrahydrofuran were added, and the mixture was again stirred for 30 minutes. A solution of 1.77 g (2.12 mmol) of bis(perfluorononyl) azodicarboxylate in 2 ml of tetrahydrofuran was slowly added dropwise (exothermic reaction) and stirred at room temperature for 2 hours. It was not possible to convert the suspension into a solution by adding 1 ml of dimethylformamide. The reaction mixture was filtered with suction (precipitate corresponds to 408 mg of 4,5-diphenylpyrimidin-2-ol). The filtrate was filtered twice through a FluoroFlash cartridge and washed with methanol/water=4/1, and the filtrate was concentrated. The residue was separated on a silica gel column (heptane/ethyl acetate, 10 minutes 100% heptane, gradient from 0% to 45% ethyl acetate in 45 minutes). 28 mg (4%) of the desired product were obtained.

Provenance & Evidence