Triethylamine → HCID 67172912, compound

Participants

Reaction Conditions

Reaction Steps

4-bromo-2-chlorobenzaldehyde (2B1) (4.56 mmol, 1.0 g) and glycine methyl ester hydrochloride (2C2) (4.56 mmol, 572 mg) were dissolved in ethanol (15 ml) under nitrogen with stirring and triethylamine (135 mmol, 19.0 ml, 13.7 g) was added. The reaction mixture was heated to 50° C. for 1 hour, then evaporated to dryness and the residue taken up in methanol (15 ml) and cooled in an ice bath. Sodium borohydride (5.01 mmol, 0.190 g) was added portionwise and stirring continued until no starting material remained as determined by TLC. The reaction mixture was concentrated to dryness and partitioned between DCM and water and the phases separated. The organic layer was dried over sodium sulphate, filtered and concentrated before purification on silica eluting with 15% EtOAc/heptane to yield methyl 2-(4-bromo-2-chlorobenzylamino)acetate (2C3) 420 mg (31%); 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H) 7.38 (d, 1H) 7.31 (d, 1H) 3.86 (s, 2H) 3.73 (s, 3H) 3.43 (s, 2H).

Provenance & Evidence