Iodine → HCID 66673659, compound

Participants

Reaction Steps

Add dropwise via an addition funnel a solution of iodine (727 mg, 2.86 mmol) in tetrahydrofuran (5 mL) over 15 min to a mixture of N—[(R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-yl]-2-methoxy-acetamide (500 mg, 1.59 mmol) and sodium borohydride (217 mg, 6.05 mmol) in tetrahydrofuran (5 mL). Heat the colorless mixture at reflux overnight, then cool to room temperature and slowly quench with MeOH until no foaming is observed. Concentrate the material in vacuo. Add 1N NaOH (20 mL) to the residue and extract the mixture with dichloromethane (3×20 mL). Dry the combined organics over Na2SO4, filter, and concentrate to dryness. Purify using chromatography (0 to 10% MeOH/CH2Cl2) to afford 120 mg (26%) of the title compound. LC-MS/ES m/z (79Br) 286.2 [M+H]+.

Provenance & Evidence