[H-].C([Al+]CC(C)C)C(C)C.C(OC([N:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]([NH:27][C@H:28]([C:32](OC)=O)[CH:29]([CH3:31])[CH3:30])=[O:26])[CH2:20][CH2:19]1)=O)(C)(C)C>C1(C)C=CC=CC=1.ClCCl>[CH:29]([C:28]1[NH:27][C:25](=[O:26])[N:24]([CH:21]2[CH2:20][CH2:19][NH:18][CH2:23][CH2:22]2)[CH:32]=1)([CH3:30])[CH3:31]Diisobutylaluminum hydride (1M, 0.520 mL, 0.520 mmol) was added to a solution of methyl N-{[(1-tert-butoxycarbonylpiperidin-4-yl)amino]carbonyl}valinate (155 mg, 0.434 mmol) in toluene (3 mL) and dichloromethane (3 mL) at −78° C. and stirred for 30 min and then warmed to ambient temperature. After 1 h, the reaction was quenched with 1 N saturated potassium sodium tartrate solution (3 mL) and extracted with dichloromethane (2×). The combined organic extracts were dried over sodium sulfate, filtered, concentrated. The crude material was dissolved in dichloromethane (5 mL) and treated with trifluoroacetic acid (5 mL). After 30 min, the reaction was concentrated to give the title compound. MS 210.1 (M+1)
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