Toluene → HCID 69300175, compound

Participants

Reaction Steps

In 10 mL of toluene, 200 mg (0.35 mmol) of 2-(3-benzyloxy-17-cyclopropylmethyl-4,5α-epoxy-14-hydroxy-morphinan-6β-yl)-3-hydroxy-2,3-dihydro-isoindol-1-one obtained in Example 26-1 was dissolved, and 147 mg (0.43 mmol) of (carbomethoxymethylene)triphenylphosphorane was added thereto, followed by heating the mixture to reflux for 15 hours. Thereafter, aqueous saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting mixture was extracted with chloroform. Organic layers were combined, washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography to obtain the captioned compound as 33 mg of low polarity component and 38 mg of high polarity component (yields: 15% and 17%, respectively).

Provenance & Evidence