Acetic Acid → Ethyl 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)amino)acetate

Participants

Reaction Steps

A mixture of the chlorhydrate salt of ethyl 2-amino-2-(2,6-dimethoxyphenyl)acetate (8.43 mmol), commercially available 4-(trifluoromethoxy)benzaldehyde (1.603 g; 8.43 mmol), DIPEA (2.179 g; 16.86 mmol), NaBH(OAc)3 (2.633 g; 11.80 mmol), and acetic acid (506 mg; 8.43 mmol) in anh. DCE (9 ml) was stirred at rt, under nitrogen, for 16 h. 1 M aq. NaOH (17 ml) was added, and the separated aq. layer was further extracted with DCM (3×50 ml). The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded ethyl 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)amino)acetate. LC-MS (conditions D): tR=0.92 min.; [M+H]+: 414.05 g/mol.

Provenance & Evidence