反応 #44771

反応方程式

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

収率 45.9%

溶媒

dichloroethane

反応条件

後処理

1. 1
   workup.ADDITIONwere added sequentially at ambient temperature
2. 2
   抽出extracted with EtOAc
3. 3
   その他The combined organic extracts were dried
4. 4
   濃縮concentrated
5. 5
   その他Purification by flash chromatography

実験手順

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.

出典