Binap, (A+-)- → 5-(1-Benzyl-pyrrolidin-3-ylamino)-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

Participants

Reaction Steps

3-Amino-1-benzyl-pyrrolidine (57 mg, 0.325 mmol), 5-Bromo-7-methyl-2-(4-trifluoromethoxybenzyl)-2,3-dihydro-isoindol-1-one (100 mg, 0.25 mmol), NaOtBu (168 mg, 1.75 mmol), BINAP (16 mg, 0.025 mmol) and Pd2(dba)3 (23 mg, 0.025 mmol) were dissolved in anhydrous toluene (5 mL). The mixture was immersed in a 110° C. oil bath. After eighteen hours, the reaction was cooled and poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The compound was purified by column chromatography (50% EtOAc/Hexanes) to provide the title compound as a yellow gum (87 mg, 70%). 1H NMR (300 MHz, CDCl3): δ 7.24-7.34 (m, 7H), 7.18 (d, 2H), 6.34 (d, 2H), 4.72 (s, 2H), 4.33 (d, 1H), 4.12 (s, 2H), 4.04 (m, 1H), 3.64 (collapsed dd, 2H), 2.75-2.83 (m, 2H), 2.66 (s, 3H), 2.58 (dd, 1H), 2.45 (ddd, 1H), 2.32-2.42 (m, 1H), 1.67-1.70 (m, 1H).

Provenance & Evidence