반응 #44017

반응 방정식

trans-2,6-Dimethylpiperidin-4-one

trans-2,6-dimethylpiperidin-4-one

triethylamine

4-chlorobenzenesulfonyl chloride

→

product 94

trans-1-(4-chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 24 hr
2. 2
   기타partitioned between water (300 mL) and CH2Cl2 (300 mL)
3. 3
   세척The organic layer was washed with 0.2 N citric acid, water, brine
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   기타the solvent evaporated
7. 7
   기타The residue (6.7 g) was purified by flash chromatography
8. 8
   세척eluting with EtOAc-hexane (1:3) mixture

실험 절차

trans-2,6-Dimethylpiperidin-4-one (93; 5.2 g, 39 mmol) was dissolved in CH2Cl2 (100 mL) and triethylamine (22 mL, 155 mmol) was added. The solution was stirred and treated with 4-chlorobenzenesulfonyl chloride (9.2 g, 43 mmol). The mixture was stirred for 24 hr and then partitioned between water (300 mL) and CH2Cl2 (300 mL). The organic layer was washed with 0.2 N citric acid, water, brine, dried over Na2SO4, filtered and the solvent evaporated. The residue (6.7 g) was purified by flash chromatography, eluting with EtOAc-hexane (1:3) mixture to yield 3.6 g (35%, 2 steps) of product 94.

출처