反応 #44017

反応方程式

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

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred for 24 hr
2. 2
   その他partitioned between water (300 mL) and CH2Cl2 (300 mL)
3. 3
   洗浄The organic layer was washed with 0.2 N citric acid, water, brine
4. 4
   乾燥dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   その他the solvent evaporated
7. 7
   その他The residue (6.7 g) was purified by flash chromatography
8. 8
   洗浄eluting with EtOAc-hexane (1:3) mixture

実験手順

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.

出典