Methyl iodide → HCID 23355091, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of diisopropylamine (0.42 ml, 3.0 mmol) in THF (10 ml) at 0° C. was added butyllithium (1.6M; 1.87 ml, 3.0 ml) in hexane followed after 5 minutes by a solution of 1-(1-adamantyl)-3-(3-pyridyl)propan-1-one in THF (8 ml). After stirring for a further 20 min at 0° C., methyl iodide (0.19 ml, 3.0 mmol) was added dropwise and the solution was allowed to attain room temperature. After 1 hr the mixture was partitioned between ether and water. The ether extracts were dried (Na2CO3) and concentrated. Chromatography on elution with petrol-ether-triethylamine 100:50:1 afforded the title compound (0.62g, 73%), which crystallised from pentane, m.p 69-70 C; IR νmax 1696 cm-1 ; 1H-NMR (CDCl3) δ1.06 (3H,d,J 6.7 Hz, CHCH3) 1.51-1.72 (12H, m, adamantyl CH2), 1.96 (3H, s, adamantyl CH), 2.57 and 2.92 (2H, m, CHCH2), 3.28 (1H, m, CHCH3), 7.18 (1H, m, Py 5-H), 7.43 (1H, m, Py 4-H), 8.43 (2H, m, Py 6-H and 2-H); MS m/z 283 (M+). Anal. Calcd: C, 80.52; H, 8.89; N, 4.94. Found: C, 80.56; H, 8.95; N, 4.91%.

Provenance & Evidence