[CH:1]1([CH2:5][CH:6]=[N:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3][CH2:2]1.[Mg+2].[Br-].[Br-].C[Si](C)(C)[O:20][C:21]([O:29][CH2:30][CH3:31])=[C:22]([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:8]([NH:7][CH:6]([CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[C:22]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[C:21]([O:29][CH2:30][CH3:31])=[O:20])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1N-(2-cyclobutylethylidene)-1-phenylmethanamine (1.00 g, 5.3 mmol) was dissolved in 23 mL toluene, MgBr2.0Et2 (2.07 g, 8.0 mmol) was added and the mixture was stirred at room temperature for 15 minutes. Trimethyl(1,2,2-triethoxyvinyloxy)silane (1.83 g, 7.4 mmol) was added, and the mixture was stirred at room temperature. After 3 hours, the reaction was quenched with water (30 mL) and acidified to pH=2 with hydrochloric acid. The organic phase was washed with sat. NaHCO3, dried over Na2SO4 and the solvent was removed under vacuum to yield the crude product. Column chromatography (silica, cyclohexane:ethyl acetate 10:1) yielded 1.1 g ethyl 3-(benzylamino)-4-cyclobutyl-2,2-diethoxybutanoate.
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