1-Azatricyclo(3.3.1.1,3,7)decan-4-one → HCID 15214081, compound

Participants

Reaction Conditions

Reaction Steps

Azaadamantan-4-one (3.76 g, 24.9 mmol; see Becker, D. P.; Flynn, D. L. Synthesis 1992, 1080-1082.) and p-toluenesulfonylmethyl isocyanide (TOSMIC, 6.38 g, 32.3 mmol) were dissolved in a mixture of 1,2-dimethoxyethane (87 mL) and ethanol (3.2 mL) and chilled to −78° C. To the reaction mixture was added potassium tert-butoxide (6.70 g, 59.7 mmol) over a period of 1 minute. The cooling bath was removed and the reaction mixture was stirred at 25° C. for 5 hours and then heated at 40° C. for 0.5 hour. The reaction mixture was cooled and filtered through a glass frit. The filtrate was concentrated, and the residue was purified by silica gel chromatography (10% concentrated NH4OH in acetonitrile, Rf=0.25) to afford the title compound. An aliquot of the solid was then dissolved in 10:1 ether/methanol and treated with fumaric acid (10 mg/mL solution in 10:1 ether/methanol). The precipitate was filtered and dried under vacuum to afford the title compound as a fumarate for characterization: 1H NMR (500 MHz, methanol-d4) δ 2.07-2.14 (m, 2H), 2.22-2.32 (m, 3H), 2.47 (s, 2H), 3.49-3.56 (m, 5 H), 3.59-3.66 (m, 2 H), 6.70 ppm (s, 2.8 H; C4H4O4); MS (DCI/NH3) m/z 163 (M+H)+; Anal. Calcd. for C10H14N2.1.45C4H4O4: C, 57.41; H, 6.04; N, 8.48. Found: C, 57.26; H, 6.04; N, 8.87.

Provenance & Evidence