Trimethylsilyl iodide → 1-(2-chlorophenyl)-5-[(1S,2S)-2-hydroxycyclohexyl]-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

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Reaction Steps

The starting material for this example, namely 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one, was prepared by following the methods described in Scheme 2 and Examples 12–19, using (1S,2S)-2-(benzyloxy)cyclohexylamine as R4NH2 (Scheme 2). Then, a sample of 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.36 mmol) was dissolved in methylene chloride (5 mL). Trimethylsilyl iodide (0.054 mL, 0.396 mmol) was added dropwise and the solution was stirred at rt for 18 h. The solvent was removed and the crude material was purified by silica gel column, eluting with methylene chloride followed by methanol. The product was isolated as a white solid (40.0 mg, 24%). LC-MS m/z (MH+) 465.3, retention time 3.23 min (method 1).

Provenance & Evidence