Hydrochloric Acid → HCID 57878312, compound

Participants

Reaction Steps

(R)-5′-Amino-3-methyl-spiro[imidazolidine-4,2′-indane]-2,5-dione (0.500 g, 2.16 mmol, described in Intermediate 8) and 2-dimethylaminomethylene-1,3-bis(dimethylammonio)propane bis(tetrafluoroborate) (1.77 g, 4.97 mmol) were suspended in glacial acetic acid and the mixture was heated to reflux for 20 h. The mixture was allowed to cool to ambient temperature before the bulk of the acetic acid was removed in vacuo. THF (10 mL) and 1 N aqueous HCl (10 mL, 10 mmol) were added and the mixture was stirred at ambient temperature for 2.5 h. The mixture was then poured into a separatory funnel containing CHCl3 (150 mL) and saturated aqueous NaHCO3 (30 mL). The aqueous layer was extracted once with CHCl3 (100 mL) and the combined organics were dried over Na2SO4. Filtration to remove drying agent gave a solution which was concentrated in vacuo to give a yellow residue. The impure product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:1 to 94:6, to give the title compound. MS: m/z=296 (M+1).

Provenance & Evidence