Reaktion #1179331

Reaktionsgleichung

(Trimethylsilyl)diazomethane

2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylic acid

→

methyl 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylate

Ausbeute 88.0%

Lösungsmittel

toluene

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with the dropwise addition of acetic acid
2. 2
   Sonstigeuntil bubbling
3. 3
   workup.ADDITIONthe reaction mixture was diluted with EtOAc (100 mL) and water (100 mL)
4. 4
   SonstigeThe organic layer was removed
5. 5
   Extraktionthe aqueous further extracted with EtOAc (2×50 mL)
6. 6
   WaschenThe combined organics were washed with sodium hydrogen carbonate solution (100 mL), water (100 mL), brine (100 mL)
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated

Vorschrift

(Trimethylsilyl)diazomethane, 2M in hexanes (4.19 ml, 8.38 mmol) was added dropwise to 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylic acid (1.28 g, 4.19 mmol) in toluene (12 ml) and methanol (3.00 ml) at 25° C. over a period of 2 mins under nitrogen. The resulting solution was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with the dropwise addition of acetic acid until bubbling ceased, then the reaction mixture was diluted with EtOAc (100 mL) and water (100 mL). The organic layer was removed and the aqueous further extracted with EtOAc (2×50 mL). The combined organics were washed with sodium hydrogen carbonate solution (100 mL), water (100 mL), brine (100 mL) and dried over MgSO4, filtered and evaporated to afford methyl 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylate (1.182 g, 88%) as a yellow solid. This was used directly with no further purification.

Quelle