Sodium Carbonate → tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

HRID 1993669노트

반응식

HRID 1993669 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1>C(O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 12682914-Amino-1-Boc-piperidine

생성물 1

HCID 53255493tert-Butyl 4-(5-nitropyridine-2-ylamino)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Dissolve N-Boc-4-aminopiperidine (0.9 g, 4.8 mmol) in dry ethanol and add solid sodium carbonate (0.8 g, 7.9 mmol) at 0° C., followed by 2-chloro-5-nitro-pyridine (0.6 g, 3.9 mmol). Stir the solution at room temperature overnight, then heat the solution at 9° C. for 6 hours. Stir at room temperature overnight. Evaporate the solvent under reduced pressure and partition the crude mixture between EtOH and water. Extract with EtOAc and wash the organic layer with saturated aq. sodium chloride solution. Combine organic layers and dry over MgSO4. Filter and evaporate the solvent in order to obtain 4-(5-Nitro-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester.

후처리

  1. temperatureheat the solution at 9° C. for 6 hours
  2. stirringStir at room temperature overnight
  3. customEvaporate the solvent under reduced pressure
  4. custompartition the crude mixture between EtOH and water
  5. extractionExtract with EtOAc
  6. washwash the organic layer with saturated aq. sodium chloride solution
  7. dry with materialCombine organic layers and dry over MgSO4
  8. filtrationFilter
  9. customevaporate the solvent in order

출처 및 근거

ORD 기록
ord-5889c8e2a7d948fdb556c226a1f8094e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652015B2

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