تفاعل #1435747

معادلة التفاعل

TFA

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

morpholine

sodium cyanoborohydride

→

4-Piperidin-4-yl-morpholine

المذيبات

ethanol

methylene chloride

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature over night
2. 2
   أخرىthe reaction was quenched with addition of water (4 mL)
3. 3
   workup.STIRRINGThe mixture was stirred for 30 minutes
4. 4
   ترشيحthe white solid was filtered out
5. 5
   أخرىthe filtrate was evaporated
6. 6
   أخرىThe residue was partitioned between ether and water
7. 7
   أخرىthe organic layer was separated
8. 8
   تجفيفdried with sodium sulfate
9. 9
   أخرىRemoval of solvent
10. 10
    أخرىgave a white solid which
11. 11
    workup.STIRRINGThe solution was stirred at room temperature for 1 hour
12. 12
    أخرىthe solvent was removed
13. 13
    أخرىto give a white solid

الإجراء التجريبي

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.

المصدر