Iodine → HCID 57495610, compound

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (200 mg) was added to THF (10 mL), followed by cyclopropyl-cyclopropylamino-acetic acid (1 g of the material obtained in step B]). The mixture was cooled to 0° C. and a solution of iodine (558 mg) in THF (5 mL) was added carefully drop by drop over a period of 30 minutes. Vigorous hydrogen evolution was observed. The mixture was stirred at 0° C. for 30 minutes and then heated to reflux for 2 hours. The mixture was cooled and quenched with methanol until a clear solution was obtained. The solution was stirred for 30 minutes and then evaporated in vacuo. The residue was treated with 20% KOH (10 mL) and extracted with DCM. The combined organic extracts were dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography using methanol/ethyl acetate 2:3 as an eluent to give 2-cyclopropyl-2-cyclopropylamino-ethanol (73 mg) as a colorless oil. MS (ESI): 142.2 (MH+).

Provenance & Evidence