HCID 11662369, compound → HCID 11639726, compound

Participants

Reaction Steps

8′-{[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′pyrimido[1,2-a]indole] (0.765 g, 1.70 mmol) was added portion-wise to cold concentrated H2SO4 (10 mL) over a period of 0.5 hr. with cooling in an ice bath. The bath was removed and the reaction stirred at room temp for 1 hr. The reaction mixture was gradually added to ice over a period of 15 min. and was basified to pH 11.1 with concentrated NH4OH keeping the temperature cold by the addition of ice and an external ice bath. The reaction was filtered and the collected solid was dissolved in CH2Cl2, dried over Na2SO4 and concentrated to give the title compound as a bright yellow solid (0.601 g, 90% yield). NMR (400 MHz, DMSO-d6): consistent. IR: consistent. MS: (ES+) m/z 392 [M+H]. Opt. Rot: +74.84 (calculated) in CH2Cl2 (1% concentration) wavelength 589, 25° C.; m.p.: 161-164° C.

Provenance & Evidence