1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate → Tert-butyl 7-(2-chlorophenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1-tert-Butyl 2-methyl 2-{2-[(2-chlorophenyl)amino]ethyl}pyrrolidine-1,2-dicarboxylate, was dissolved in anhydrous THF (4 mL) and cooled to 0° C. To this cooled solution was added isopropylmagnesium chloride in THF (2.0 M, 2 mL). The reaction vial was then sealed and heated to 64° C. and stirred for 18 h. The reaction mixture was then diluted with EtOAc and quenched by the addition of water. The crude mixture was filtered through a pad of diatomaceous earth and the filter pad was washed several times with EtOAc. The organic and aqueous layers of the filtrate were separated. The aqueous phase was extracted with EtOAc (3×10 mL) and the combined organic phases were washed with brine (2×5 mL), then dried (NaSO4), filtered, and concentrated in vacuo to afford the desired product. LC-MS: 251.1 (M−Boc+2H)+ and 295.1 (M−t-Bu+2H)+.

Provenance & Evidence