8-Oxabicyclo[3.2.1]oct-6-en-3-one → HCID 178456493, compound

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Reaction Steps

To a stirred solution of 1,3-dipropyl-7-pyrrolidin-1-ylmethyl-3,7-dihydro-purine-2,6-dione (Example 48) (522 mg, 1.63 mmol) in THF (50 ml) at −78° C. was added n-BuLi (1.55 M in hexanes, 1.2 eq, 1.3 ml). The color of the resulting yellow mixture deepened to orange-red and was stirred at this temperature for 0.5 h. A solution of 8-oxa-bicyclo[3.2.1]oct-6-en-3-one (1.1 eq, 222 mg, 1.79 mmol) in THF (4 ml) was added via syringe over a period of 20 minutes. The mixture was held at −78° C. for 2 h and allowed to reach ambient temperature overnight (12 h). The reaction mixture was partitioned between saturated aqeuous NH4Cl (20 ml) and EtOAc (20 ml) and the aqueous phase was extracted with EtOAc (20 ml). The combined organic extracts were washed with saturated aqeuous NaCl (20 ml), dried (MgSO4), filtered and concentrated in vacuo. The resulting orange oil was purified by chromatography on silica using 5% MeOH in CH2Cl2 as eluent to give a clear oil that solidified upon standing (50 mg, 8%).

Provenance & Evidence