Triethylamine → Benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate

HRID 20221

반응식

HRID 20221 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.Br[CH:26]([CH3:33])[CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31]>C1COCC1>[O:31]=[C:30]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:33][N:1]1[CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 178466404-Amino-1-N-Cbz-piperidineHCID 198952945-Bromohexanoyl chloride

생성물 1

HCID 68418576Benzyl 4-(2-oxoazepan-1-yl)piperidin-1-carboxylate수율 10%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of benzyl 4-aminopiperidin-1-carboxylate (1.7 g) and triethylamine (1.1 mL) in THF (40 mL) was added dropwise 5-bromohexanoyl chloride (1.1 mL), and the mixture was stirred at 0° C. for 2 hours. The solvent was distilled off under reduced pressure and the residue was diluted with water, and extracted with ethyl acetate. The extract was washed with an aqueous 5% citric acid solution and a saturated saline solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in DMF (40 mL), and cooled at 0° C., sodium hydride (60% in oil; 0.60 g) was added thereto, and the mixture was stirred at 0° C. for one hour, at room temperature for one hour and at 80° C. for 15 hours. The solvent was distilled off under reduced pressure, the residue was diluted with water, and the solution was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated saline solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1 to 5/1) to obtain the title compound (0.25 g, 10%) as a yellow oil.

후처리

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous 5% citric acid solution
  5. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe residue was dissolved in DMF (40 mL)
  8. temperaturecooled at 0° C.
  9. additionsodium hydride (60% in oil; 0.60 g) was added
  10. stirringthe mixture was stirred at 0° C. for one hour, at room temperature for one hour and at 80° C. for 15 hours
  11. distillationThe solvent was distilled off under reduced pressure
  12. additionthe residue was diluted with water
  13. extractionextracted with ethyl acetate
  14. washThe extract was washed with water and saturated saline solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. distillationthe solvent was distilled off under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1 to 5/1)

출처 및 근거

ORD 기록
ord-8135a7c7eccb4f2a822ae27c502aa13d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745623B2

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