C(NC(C)C)(C)C.[Li]CCCC.[Li+].CC([N-]C(C)C)C.[CH2:21]([N:23]([CH2:39][CH3:40])[C:24](=[O:38])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][N:32]1[C:36]([I:37])=[CH:35][N:34]=[CH:33]1)[CH3:22].[C:41]1(=[O:45])[CH2:44][CH2:43][CH2:42]1>C1COCC1.O.C(O)(=O)C>[CH2:39]([N:23]([CH2:21][CH3:22])[C:24](=[O:38])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH:31]([C:41]1([OH:45])[CH2:44][CH2:43][CH2:42]1)[N:32]1[C:36]([I:37])=[CH:35][N:34]=[CH:33]1)[CH3:40]To a solution of diisopropylamine (0.38 g, 3.76 mmol) in THF (25 mL) at −78° C. under nitrogen is added n-BuLi (2.5M in hexanes, 1.50 mL, 3.75 mmol) and the mixture is warmed to 0° C. After 15 min, the LDA solution is cooled to −78° C. and a solution of N,N-diethyl-2-(5-iodo-imidazol-1-ylmethyl)-benzamide (1.00 g, 2.51 mmol) in THF (5 mL) is added over 10 min. Fifteen min after the end of addition, cyclobutanone (0.90 g, 12.53 mmol) in THF (2 mL) is added to the brown solution. After 1.5 h, 10% acetic acid in water is added. The organic phase is washed with saturated aqueous sodium bicarbonate and the combined organic phase is dried over MgSO4, filtered through a cotton plug and concentrated in vacuo. The residue is purified by silica gel flash chromatography (elution with dichloromethane-methanol, 49:1 to 97:3) to N,N-diethyl-2-[(1-hydroxy-cyclobutyl)-(5-iodo-imidazol-1-yl)-methyl]-benzamide; MS (ESI) m/z 454.2 (M+H).
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