Methyl iodide → HCID 60141609, compound

Participants

Reaction Steps

(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester (100 mg, 0.32 mmol) was dissolved in DMF (3 mL). Then, molecular sieves (4 A), silver(I)oxide (355 mg, 1.53 mmol) and methyl iodide (0.40 ml, 6.38 mmol) was added and the black suspension stirred at room temperature for 48 hour. The reaction mixture was filtrated through celite and the filtrate evaporated. The crude yellow residue was subjected to silica gel flash chromatography (ISCO Companion CombiFlash; 40 g Gold silica gel cartridge, heptane/ethyl acetate gradient; ethyl acetate: 2% (2 min), 2-20% (3 min), 20% (8 min), 20-30% (2 min), 30% (8 min), 30-50% (3 min) and 50% (8 min) to yield (3aR,4S,7aR)-4-methoxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester (15 mg, 0.04 mmol, 14% yield) as colorless oil. MS [2M+Na]677; RT=8.147 min HPLC Method III

Provenance & Evidence