Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → Methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate

Participants

Reaction Steps

A solution of 1.98 g (12.2 mmol) of methyl (Z)-cinnamate and 5.80 g (24.4 mmol) N-(methoxymethyl)-N-(trimethylsilylmethyl)-benzylamine in 30 mL of CH2Cl2 at 0° C. was treated with 20 drops of trifluoroacetic acid and stirred cold for 1 h. The reaction mixture was partitioned between 200 mL of ether and 100 mL of sat'd NaHCO3 and the layers were separated. The organic layer was washed with 100 mL of sat'd NaCl, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 150 g of silica gel using 20:1 v/v CH2Cl2/ether as the eluant afforded 2.61 g (72%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.83 (t, J=8.7, 1H), 3.09-3.19 (m, 6H), 3.16 (s, 3H), 3.46-3.51 (m, 1H), 3.73-3.79 (m, 3H), 7.19-7.42 (1OH). Mass Spectrum (NH3 -CI): m/z 296 (M+1).

Provenance & Evidence