Lithium tri-s-butylborohydride → HCID 131733492, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 416 (1.6 g, 4.9 mmol) and anhydrous THF (50 mL) cooled to −78° C. was added dropwise L-selectride (1.0 M, 15 mL) and then the reaction was stirred at −78° C. for 3 h. The reaction was quenched with H2O (30 mL). The mixture was extracted with EtOAc (3×100 mL) and the extract was washed with brine (3×30 mL). The organic phases were dried (Na2SO4), filtered and concentrated. LC-MS indicated about 9:1 of two isomers. The residue was purified by reverse phase column chromatography using a MeCN/5% aqueous NH4OH (0 to 35%) to afford 0.56 g (35%) of cis-(±)-tert-butyl 3-(4-chloro-3-fluorophenoxy)-4-hydroxy-pyrrolidine-1-carboxylate (418). LC-MS (ESI) m/z 276 (M+H-56).

Provenance & Evidence