Reacción #44771

Ecuación de reacción

1,1-dimethylethyl 2-(aminomethyl)-1-pyrrolidinecarboxylate

methyl 4-formylbenzoate

acetic acid

sodium triacetoxyborohydride

sodium bicarbonate

→

1,1-dimethylethyl 2-[[[[4-(methoxycarbonyl)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylate

Rendimiento 45.9%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added sequentially at ambient temperature
2. 2
   Extracciónextracted with EtOAc
3. 3
   OtroThe combined organic extracts were dried
4. 4
   Concentraciónconcentrated
5. 5
   OtroPurification by flash chromatography

Procedimiento

A solution of 1,1-dimethylethyl 2-(aminomethyl)-1-pyrrolidinecarboxylate (1000 mg, 5 mmol) and methyl 4-formylbenzoate (820 mg, 5 mmol) in dichloroethane was stirred as acetic acid (450 mg, 7.5 mmol) and sodium triacetoxyborohydride (1271 mg, 6 mmol) were added sequentially at ambient temperature. After stirring at ambient temperature for 17 hours, treated with a saturated aqueous solution of sodium bicarbonate and extracted with EtOAc. The combined organic extracts were dried and concentrated. Purification by flash chromatography afforded 1,1-dimethylethyl 2-[[[[4-(methoxycarbonyl)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylate (800 mg), 1H NMR (CDCl3) 7.98 (d, 2H), 3.37 (d, 2H), 3.91 (s, 3H), 3.82 (s, 2H), 3.36 (m, 2H), 2.72 (m, 1H), 1.82 (m, 3H), 1.44 (m, 2H) ppm.

Fuente