Trimethylsilyl iodide → Rel-n-(2-{[(3r,4r)-4-(allyloxy)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl rel-(3R,4R)-3-(allyloxy)-4-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidine-1-carboxylate (575.6 mg, 1.13 mmol) in acetonitrile (5 mL) at 0° C. was added TMSI (1.3 mL, 9.04 mmol) dropwise. The reaction mixture was stirred at 0° C. for 2 h and room temperature for 3 h. The reaction was quenched by adding HCl (1N, 15 mL). The mixture was extracted from with EtOAc (15 mL×3). The aqueous phase was neutralized with NaOH (1N) to pH=10. DCM/isopropanol (4:1, 10 mL×3) was used to extract from the aqueous layer. The organic layers then were combined, dried over MgSO4, filtered, concentrated under reduced pressure to afford rel-N-(2-{[(3R,4R)-4-(allyloxy)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide which was used without further purification (115.6 mg).

Provenance & Evidence