反应 #1435747

反应方程式

TFA

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

morpholine

sodium cyanoborohydride

→

4-Piperidin-4-yl-morpholine

溶剂

ethanol

methylene chloride

THF

反应条件

后处理

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature over night
2. 2
   其他the reaction was quenched with addition of water (4 mL)
3. 3
   workup.STIRRINGThe mixture was stirred for 30 minutes
4. 4
   过滤the white solid was filtered out
5. 5
   其他the filtrate was evaporated
6. 6
   其他The residue was partitioned between ether and water
7. 7
   其他the organic layer was separated
8. 8
   干燥dried with sodium sulfate
9. 9
   其他Removal of solvent
10. 10
    其他gave a white solid which
11. 11
    workup.STIRRINGThe solution was stirred at room temperature for 1 hour
12. 12
    其他the solvent was removed
13. 13
    其他to give a white solid

实验过程

To a stirred solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (Aldrich, 3.0 g, 15 mmol) in THF (25 mL), morpholine (Aldrich, 1.56 g, 18 mmol) and Ti(OiPr)4 (Aldrich, 5.58 mL) were added successively and the mixture was stirred at room temperature for 1 hour. Then, 15 mL of ethanol was added and followed by sodium cyanoborohydride (0.63 g, 10.05 mmol). The resulting mixture was stirred at room temperature over night and the reaction was quenched with addition of water (4 mL). The mixture was stirred for 30 minutes and the white solid was filtered out and the filtrate was evaporated. The residue was partitioned between ether and water and the organic layer was separated and dried with sodium sulfate. Removal of solvent gave a white solid which was treated with 40 mL of 50% TFA in methylene chloride. The solution was stirred at room temperature for 1 hour and the solvent was removed. The residue was lyophilized to give a white solid. 5.48 g, 98%. MS (m+H)+: 171.

来源