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

HRID 1993669ノート

反応式

HRID 1993669 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5889c8e2a7d948fdb556c226a1f8094e
出典データセット
uspto-grants-2010_01
特許番号
US07652015B2

反応ノート

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