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Sulfuric Acid → 1-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine

HRID 497336
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HRID 497336 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:15]([C:23]([OH:25])=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)(O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[OH-].[Na+].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.S([O-])(O)(=O)=O.[K+]>C(Cl)(Cl)Cl.O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([CH:15]([C:23]([OH:25])=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 516920Potassium bisulfateHCID 223186301-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-4-hydroxypiperidine

생성물 1

HCID 223186591-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine
수율 94.8%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

실험 절차

20.0 g of 1-t-Butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-4-hydroxypiperidine was suspended in 40 ml of chloroform, and 40 ml of conc. sulfuric acid was added dropwise with ice-cooling. The reaction solution was refluxed with heating for 3 hours and, after ice-cooling, 250 ml of 4M sodium hydroxide solution, 200 ml of 1,4-dioxane and 14.8 g of di-t-butyldicarbonate were added. After stirring at room temperature for 30 minutes, the reaction solution was made acidic with potassium hydrogensulfate, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (Wako-gel C-200, chloroform:methanol=10:1) to give 18.0 g of 1-t-butoxycarbonyl-4-[carboxy-(4-fluorophenyl)methyl]-3,6-dihydro-2H-pyridine as an oil.

후처리

  1. temperaturecooling
  2. temperatureThe reaction solution was refluxed
  3. temperaturewith heating for 3 hours
  4. temperatureafter ice-cooling
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by a silica gel column chromatography (Wako-gel C-200, chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-a17445d5aa0d4d4bb8034fd3ceece422
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06949552B2

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