Methyl iodide → HCID 59178184, compound

Participants

Reaction Steps

Methyl (3S,4R)-3,4-dihydroxycyclopentanecarboxylate (0.481 g, 3 mmol), freshly prepared silver oxide (0.348 g, 1.500 mmol) and methyl iodide (0.375 ml, 6.00 mmol) were combined in DMF and allowed to stir for 3 hrs. The reaction mixture was filtered through celite and washed with 15 ml of ether. The organic filtrate was washed 2× with brine, dried over sodium sulfate and evaporated. Purification by silica gel chromatography eluting with 20-40% acetone hexane gave the title compound. 1H NMR (500 MHz, CDCl3) δ 2.01-2.18 (m, 4H), δ 2.48 (s, br, 1H), δ 2.77 (m, 1H), δ 3.40 (s, 3H) δ 3.6-3.65 (m, 1H), δ 3.71 (s, 3H), δ 4.10 (m, 1H)

Provenance & Evidence