반응 #1123954

반응 방정식

4-hydroxy-piperidine-1-carboxylic acid isopropyl ester

4,6-dichloro-5-methyl-pyrimidine

→

4-(6-chloro-5-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester

수율 98.3%

용매

THF

potassium tert-butoxide

THF

반응 조건

후처리

1. 1
   workup.ADDITIONeverything had been added
2. 2
   농축mixture was concentrated
3. 3
   추출Residue was extracted with methylene chloride and water
4. 4
   건조Organic phases were dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

To a solution of 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (6.26 g, 33.4 mmol) and 4,6-dichloro-5-methyl-pyrimidine (5.45 g, 33.4 mmol) in 100 mL THF, 1M potassium tert-butoxide in THF (40 mL, 40 mmol) were added slowly by syringe pump. After 1 hour, everything had been added and mixture was concentrated. Residue was extracted with methylene chloride and water. Organic phases were dried over magnesium sulfate, filtered, and concentrated to give 4-(6-chloro-5-methyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester as a pale yellow solid (10.3 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 1.22-1.24 (d, 6H), 1.74-1.81 (m, 2H), 1.95-2.04 (m, 2H), 2.24 (s, 3H), 3.40-3.45 (m, 2H), 3.74-3.81 (m, 2H), 4.90-4.98 (m, 1H), 5.31-5.37 (m, 1H), 8.40 (s, 1H).

출처