Methyl iodide → HCID 53822127, compound

Participants

Reaction Steps

To a suspension of sodium hydride (80% disp. in oil, 130 mg, 4.2 mmol) in dry N,N-dimethylformamide (6 ml) under nitrogen was added dropwise a solution of (±) cis-1-(3,4-dichlorobenzyl)-2-tert-butoxycarbonylaminoindane (1.65 g, 4.2 mmol) in N, N-dimethylformamide (10 ml). After stirring the mixture for 30 minutes at room temperature, iodomethane (0.28 ml, 4.5 mmol) was added dropwise and stirring continued for a further 1 h. The reaction mixture was then poured into a large excess of sat. ammonium chloride and extracted with diethyl ether (3×40 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The residue was subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford the title compound as a colourless oil (1.02 g).

Provenance & Evidence