반응 #44500

반응 방정식

product

9-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

6-chloro-nicotinonitrile

NaH

→

titled product

9-[4-(5-Cyano-pyridin-2-yloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

용매

tetrahydrofuran

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred for another five hours
3. 3
   온도The dark brown reaction mixture was cooled (0° C.)
4. 4
   기타quenched with acetic acid (0.1 mL)
5. 5
   기타partitioned with diethyl ether and water
6. 6
   세척The organic phase was washed with water and brine
7. 7
   건조dried (MgSO4)
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타The residue was purified over silica gel using 5-80% ethyl acetate in hexanes

실험 절차

NaH (0.1 g, 60% in oil, 2.56 mmol) was added in one portion to a stirred and cooled (0° C.) solution of the product of Example 7D (0.48 g, 1.42 mmol) and 6-chloro-nicotinonitrile (0.35 g, 2.56 mmol) in tetrahydrofuran (7 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (7 mL). After the addition, the solution was warmed to room temperature and stirred for another five hours. The dark brown reaction mixture was cooled (0° C.), quenched with acetic acid (0.1 mL), and partitioned with diethyl ether and water. The organic phase was washed with water and brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 5-80% ethyl acetate in hexanes to give the titled product as a solid.

출처