Sodium hydride → (S)-3-[(S)-2-Azido-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester

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Reaction Steps

(S)-3-((S)-2-Azido-1-hydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester (1.3 g, 5.0 mmol, 1.0 eq.) was combined with DMF (18 mL). Washed and dried NaH (362 mg, 15.1 mmol, 3.0 eq.) was carefully added in 3 separate portions. The resulting mixture was stirred at room temperature for 15 minutes under nitrogen. 4-Fluorobenzotrifluoride (1.9 mL, 15.1 mmol, 3.0 eq.) was added and the mixture was stirred at 100° C. for 3 hours. The mixture was then concentrated under reduced pressure. The resulting material was dissolved in EtOAc (15 mL) and washed with water (1×15 mL). The organic layer was concentrated and purified by flash chromatography (0-100% EtOAc/hexanes) to yield (S)-3-[(S)-2-azido-1-(4-trifluoromethylphenoxy)ethyl]-pyrrolidine-1-carboxylic acid t-butyl ester (1.4 g).

Provenance & Evidence