HCID 66670645, compound → (3R,4S)-tert-Butyl 3-(bis(4-Methoxyphenyl)(phenyl)Methoxy)-4-((Methylsulfonyl)oxy)pyrrolidine-1-carboxylate

Participants

Reaction Steps

Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3 g, 16 mmol), was dissolved in 2-methyl-tetrahydrofuran (5 mL) and added dropwise to a solution of phenylmagnesium bromide (1.5 eq, 24.3 mL of a 1.0 M solution) and copper iodide (0.05 eq) at 0° C. The reaction was allowed to warm to room temperature and stir for 18 h. Reaction was cooled to 0° C. and quenched with sat. NH4Cl solution and extracted with EtOAc. Organic was washed with NaHCO3 and brine and dried over Na2SO4 and the solvent removed. Residue was purified by column chromatography on SiO2 (15-40% EtOAc/HEptane) which gave the title compound Ia as a yellow oil (3.59 g).

Provenance & Evidence