반응 #84000

반응 방정식

Dimethyl-3-oxoglutarate

methanol

ammonium formate

NaBH3CN

→

dimethyl-3-aminoglutarate

수율 75.1%

용매

HCl

Methylene chloride

반응 조건

후처리

1. 1
   기타After 24 hours the methanol was removed in vacuo
2. 2
   기타to leave a white mass
3. 3
   여과the mixture filtered
4. 4
   기타The methylene chloride was evaporated
5. 5
   기타resulting in an oil which
6. 6
   추출extracted with ether (100 ml)
7. 7
   추출The product was extracted into methylene chloride
8. 8
   건조dried over Na2SO4
9. 9
   기타evaporated

실험 절차

Dimethyl-3-oxoglutarate (10 g, 57 mmol) was added to methanol (225 ml) followed by ammonium formate (36 g, 570 mmol) and NaBH3CN (3.7 g, 57 mmol) at 25° C. After 24 hours the methanol was removed in vacuo to leave a white mass. Methylene chloride was added and the mixture filtered. The methylene chloride was evaporated resulting in an oil which was dissolved in 1N HCl (200 ml) and extracted with ether (100 ml). The ether layer was discarded and the aqueous layer was made basic using solid K2CO3. The product was extracted into methylene chloride dried over Na2SO4 and evaporated to give dimethyl-3-aminoglutarate (7.5 g). 1H NMR (d6 -DMSO) δ1.76 (bs, 2H), 2.45 (dd, 4H, J=8.08 Hz, 16.64 Hz), 3.69 (s, 6H), 5.45 (m, 1H); MS (FAB) m/e 176.0 (M+H+).

출처