Hydrochloric Acid → Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylate

HRID 1458896노트

반응식

HRID 1458896 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH:6]=1)=[O:4].Cl.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[K+].[K+]>CO.C1(C)C=CC=CC=1.[Pt]=O.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH2:6]1)=[O:4]

참가 물질

9

반응물 4

HCID 313Hydrochloric Acid2회HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22097574Methyl 2-(dimethylcarbamoyl)pyridine-4-carboxylate

생성물 1

HCID 22097566Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylate수율 96,296.297%

시약·촉매·용매 4

HCID 82844Platinum oxide (PtO)촉매HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

A mixture of compound 28 (55.4 g, 0.27 mmole), conc. HCl (16 ml) in MeOH (62 ml) was hydrogenated over platinum oxide (1 g) at 8 kg/cm2 for 24 hours. The catalyst was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting oil was used without further purification. A mixture of crude intermediate compound hydrochloride, methyl bromoacetate (61 g, 0.4 mole) and K2CO3 (73.5 g, 0.53 mole) in toluene (200 ml) was heated at 70° C. for 3 hours. After cooling the reaction mixture, H2O (200 ml) was added and extracted with EtOAc (200 ml×2). The combined organic extracts were dried over MgSO4 and concentrated down. The crude oil was purified by silica gel chromatography EtOAc as eluent to give 29 (69.8 g, 0.26 mole, 97%).

후처리

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting oil was used without further purification
  4. additionwas added
  5. extractionextracted with EtOAc (200 ml×2)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated down
  8. customThe crude oil was purified by silica gel chromatography EtOAc as eluent

출처 및 근거

ORD 기록
ord-ffe36260347a4c0aadf7e5184a368b8f
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852038

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