Triphenylphosphine → HCID 59603080, compound

Participants

Reaction Steps

To an ice cold solution of triphenylphosphine (0.17 g, 0.63 mmol) in THF (10.0 mL) was added DIAD (0.12 mL, 0.63 mmol) and the resulting solution was stirred at the same temperature for 15 min. after which a yellow precipitate was formed. 1-Boc-3-hydroxypyrrolidine (0.10 g, 0.53 mmol) was then added to the reaction mixture and allowed to stir for 20 min followed by addition of 4-bromo-2-hydroxypyridine (0.093 g, 0.53 mmol). The resulting reaction mixture was stirred for 16 h at room temperature. After completion of reaction (TLC monitoring), the reaction mixture was diluted with water and extracted with EtOAc (3×50 ml). The combined organics was dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (100-200 M, 0.5% MeOH-DCM) to obtain the desired product (0.20 g, quantitative yield). MS: 343.10 (M+H)+.

Provenance & Evidence