4-Bromoaniline → HCID 67438121, compound

Participants

Reaction Steps

To a solution of ((1S,2R)-1-formyl-2-methoxy-propyl)-carbamic acid t-butyl ester (1.92 g, 8.8 mmol) and 4-bromoaniline (1.51 g, 8.8 mmol) in dichloroethane (50 mL) was added sodium triacetoxyborohydride (3.73 g, 17.6 mmol) portionwise. After the addition, the resulting mixture was stirred at rt for over night. The reaction mixture was quenched with saturated NaHCO3, and extracted with DCM (4×40 mL). The combined DCM was dried (Na2SO4) and concentrated. The residue was subjected to ISCO (120 g column, 0-40% EtOAc in hexane over 100 min.) to give the titled compound (610 mg). MS (MH+ 373 and 375).

Provenance & Evidence