N,N,N',N'-Tetramethylethylenediamine → HCID 59770240, compound

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Reaction Steps

Add one equiv of 5,6-dihydro-benzo[d]pyrrolo[1,2-a]azepin-11-one (prepared as described in Y. Girard, J. G. Atkinson, P. C. Belanger, J. J. Fuentes, J. Rokach, C. S. Rooney, D. C. Remy, C. A. Hunt J. Org. Chem. 1983, 48, 3220) in THF to a solution of 2.5 equiv of pinicol lithio(trimethylsilyl)methaneboronate (as described in D. S. Matteson, D. Majumder Organometallics 1983, 2, 230), 1 equiv TMEDA, 2.5 equiv of tetramethylpiperidine (TMP), and THF at −78° C. Allow the solution to warm to room temperature and stir for 3.5 h before quenching with excess water. Extract well with Et2O (4×). Dry (MgSO4) and concentrate under reduced pressure. Purify the crude residue by column chromatography (5% to 10% EtOAc:hexanes) to give pure E-isomer (45%) and

Provenance & Evidence