Cyanomethylenetributylphosphorane → Methyl 1-({4-[({4-[(4-methoxybenzyl)oxy]-1,2-benzisoxazol-3-yl]oxy)methyl}piperidin-1-yl}methyl)-cyclopentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(4-methoxybenzyl)oxy]-1,2-benzisoxazol-3-ol (100 mg, 0.369 mmol, EXAMPLE 9, step 2) and methyl 1-{[4-(hydroxymethyl)piperidin-1-yl]methyl}cyclopentanecarboxylate (141 mg, 0.553 mmol, EXAMPLE 9, step 3) in toluene (2.5 mL) was added cyanomethylenetributylphosphorane (178 mg, 0.737 mmol) at room temperature. The reaction mixture was heated at 100° C. for 20 h. After cooling, the mixture was concentrated in vacuo to give a dark brown oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 5:2 to 3:2) to give 116 mg (62%) of the title compound as a white solid.

Provenance & Evidence