2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 67490991, compound

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Reaction Steps

(3S,4R)-1-Benzyloxycarbonyl-4-[1-(bromomethyl)vinyl]pyrrolidine-3-carboxylic acid tert-butyl ester (22.8 g, 53.7 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (19.5 mL, 161 mmol) were dissolved in a mixed solution of tetrahydrofuran (220 mL) and toluene (220 mL). Lithium hexamethyldisilazide (1.0 M solution in tetrahydrofuran) (80.6 mL, 80.6 mmol) was added dropwise at −78° C., and then the mixture was stirred at room temperature for five minutes. The reaction solution was extracted with a saturated ammonium chloride solution and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=24:1→2:1) to give 8.34 g of the title compound as a colorless syrup.

Provenance & Evidence