反応 #674301

反応方程式

Methanesulfonyl chloride

NH4Cl

Et3N

Et3N

methanesulfonyl chloride

tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

→

tert-butyl 2-(methylsulfonyloxy)-7-azaspiro[3.5]nonane-7-carboxylate

収率 93.1%

溶媒

DCM

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   workup.STIRRINGstirred at room temperature for 18 hrs
3. 3
   workup.STIRRINGthe mixture was stirred for another 6 h
4. 4
   workup.STIRRINGstirred at room temperature for 10 min
5. 5
   その他The layers were separated
6. 6
   抽出The aqueous phase was extracted with DCM (3×30 mL)
7. 7
   洗浄The combined organic phase were washed with HCl (1N, 20 mL) and water (20 mL)
8. 8
   乾燥were dried over anhydrous Na2SO4
9. 9
   濃縮concentrated in vacuo

実験手順

tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate (392 mg, 1.62 mmol, 1.0 equiv) was dissolved in DCM (6.0 mL). The solution was cooled to 0° C. with an external ice-bath. Et3N (237 μL, 1.706 mmol, 1.05 equiv)) and DMAP (2.0 mg, 1 mol %) were added. Methanesulfonyl chloride (132 μL, 1.706 mmol, 1.05 equiv) was then added dropwise by a syringe. The solution was stirred at 0° C. for 2.0 hrs, was then allowed to warm to room temperature and stirred at room temperature for 18 hrs. Et3N (23 μL, 0.1 equiv) and methanesulfonyl chloride (13 μL, 0.1 equiv) were added and the mixture was stirred for another 6 h. A saturated solution of NH4Cl (20 mL) was added and stirred at room temperature for 10 min. The layers were separated. The aqueous phase was extracted with DCM (3×30 mL). The combined organic phase were washed with HCl (1N, 20 mL) and water (20 mL) and were dried over anhydrous Na2SO4, concentrated in vacuo to afford 482 mg (yield 93%) of tert-butyl 2-(methylsulfonyloxy)-7-azaspiro[3.5]nonane-7-carboxylate as a white solid.

出典