Tetrahydrofuran → HCID 89649287, compound

Participants

Reaction Steps

Method B Sodium hydride (60% dispersion in oil, 26.03 mg, 0.6500 mmol) was added in two portions to a stirred solution of (5R)-2-(4-bromo-2-pyridyl)-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 19) (174.mg, 0.5900 mmol) in dry THF (8 mL) at ambient temperature under nitrogen. After stirring for 45 mins, 2-(chloromethoxy)-ethyl-trimethyl-silane (0.12 mL, 0.6500 mmol) was added dropwise over 2 minutes. The reaction mixture was stirred over the weekend. The reaction mixture was quenched by the addition of saturated ammonium chloride solution (20 ml) and the product extracted with dichloromethane twice. The combined organic extracts were passed through a hydrophobic frit and the solvent evaporated at reduced pressure. The product was purified by silica gel chromatography eluting with 0-100% ethyl acetate in iso-hexane to give a colourless solid (199 mg) (5R)-2-(4-bromo-6-methyl-2-pyridyl)-7-(2-trimethylsilylethoxymethyl)-1,7-diazaspiro[4.4]non-1-en-6-one (D42R) (199 mg);

Provenance & Evidence