Ammonium Chloride → 3,3-Dimethyl-1-[2-(2-phenethyl-4-phenyl-butyryl)-pyrrolidin-1-yl]-pentane-1,2-dione

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Reaction Conditions

Reaction Steps

To a solution of 0.18 g (0.45 mmol) of 12a in anhydrous THF (2 mL) was added dropwise at −78° C. a 1.0M solution of 2.2 mL (2.20 mmol) of 1,1-dimethylpropyl magnesium chloride in THF, and the mixture was stirred for 3 hours at −78° C. The solution was poured over saturated ammonium chloride (50 mL) and extracted with EtOAc (3×100 mL). The organic phase was dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.14 g (76.5%) of 13a as a clear oil. TLC Rf=0.5 (EtOAc/Hexanes, 1:3) 1H NMR (CDCl3, 400 MHz): δ 0.82–0.90 (m, 3H); 1.12–1.33 (m, 6H); 1.59–1.79 (m, 7H); 2.00–2.20 (m, 3H); 2.40–2.70 (t, 5H); 3.41–3.52 (m, 2H); 4.63–4.64 (m, 1H); 7.12–7.29 (m, 10H); Anal. (C29H37NO3) C, H, N.

Provenance & Evidence