Sulfuric acid magnesium salt (1:1) → Tert-butyl 2-{[(4-bromophenyl)methyl]amino}acetate

Participants

Reaction Steps

Prepared using General Procedure 12. To a stirred suspension of 4-bromobenzaldehyde (9.88 g, 53.4 mmol) and tert-butyl 2-aminoacetate hydrochloride (8.95 g, 53.4 mmol) in methyl tert-butyl ether (200 mL) were added TEA (8.19 mL, 58.7 mmol) and MgSO4. After stirring at room temperature for 18 h the reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in MeOH (200 mL), cooled to 0° C. in an ice bath and sodium borohydride (4.04 g, 107 mmol) was added portionwise. The reaction mixture was allowed to warm to room temperature and was stirred for 18 h. The reaction mixture was quenched with NaHCO3 (200 mL) and after 3 h extracted into EA (300 mL). The organic layer was washed with brine (2×200 mL), dried over MgSO4 and concentrated in vacuo to afford 11.9 g (74%) of tert-butyl 2-((4-bromobenzyl)amino)acetate INT-60. LCMS-ESI (m/z) calculated for C13H18BrNO2: 300; found 300/302 [M+H]+, tR=2.89 min (Method 10).

Provenance & Evidence