Diethyl Ether → HCID 69517166, compound

Participants

Reaction Conditions

Reaction Steps

Part A. To pyrrolidine (1.2 g, 0.018 mol) in CH2Cl2 (50 mL) at 0° C. was added 2M trimethylaluminum in heptane (9 mL, 0.018 mol) and the mixture was stirred 20 min. Ethyl-4-iodobenzoate (1 g, 3.6 mmol) was then added and the reaction was stirred 72 h. The reaction was quenched with ice and 1N HCl, extracted with CH2Cl2, and dried (MgSO4). To the crude amide was added THF (30 mL) and this solution was cooled to −20° C. To this solution TiCl4.2THF (1.2 g, 3.6 mmol) was added and stirred cold for 0.5 h. A 3M diethyl ether solution of methylmagnesium bromide (7.2 mL, 21.7 mmol) was added and the reaction was stirred 24 h at room temperature. Quenching with 30% NaOH, extracting with ethyl acetate, and drying (Na2SO4) followed by chromatography on silica gel using 0–5% MeOH in CH2Cl2 afforded 1-[1-(4-iodo-phenyl)-1-methyl-ethyl]-pyrrolidine (0.1 g, 8.8%); Mass spec (M+H)+ 316.1.

Provenance & Evidence