Borane → HCID 59803176, compound

Participants

Reaction Steps

To (R)-3-bromo-4-chloro-N-(1-phenylethyl)benzamide 72 (8.15 g, 24.1 mmol) was added borane (130 mL, 129 mmol) (1 M in THF). The reaction mixture was heated to reflux for 3 d, quenched with saturated NaHCO3, and diluted with EtOAc and water. The aqueous phase was extracted with EtOAc (1×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 10% to 40% EtOAc in hexanes) gave (R)—N-(3-bromo-4-chlorobenzyl)-1-phenylethanamine 73 (4.75 g, 60.8% yield) as a colorless oil. Mass spectrum: calculated for C15H15BrClN 323.0. found 324.1 (M++1).

Provenance & Evidence