Potassium Hydroxide → 1-(1-((tert-butoxy)carbonyl)piperidin-4-yl)-1H-pyrazole-4-carboxylic acid

HRID 512970

反応式

HRID 512970 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]([O:8]CC)=[O:7])[CH:3]=[N:2]1.[H-].[Na+].CS(O[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)(=O)=O.[OH-].[K+]>CN(C=O)C.O>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([N:2]2[CH:3]=[C:4]([C:6]([OH:8])=[O:7])[CH:5]=[N:1]2)[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

参加物

7

反応物 4

HCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

生成物 1

HCID 534858971-(1-((tert-butoxy)carbonyl)piperidin-4-yl)-1H-pyrazole-4-carboxylic acid収率 40.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of ethyl 1H-pyrazole-4-carboxylate (700 mg, 5 mmol) and NaH 60% (6 mmol) was stirred under nitrogen at 0° C. for 1 hour in dry DMF (15 mL). tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (1.53 gr, 5.5 mmol) dissolved in 4 mL of dry DMF was added and the resulting solution was heated at 100° C. overnight. Reaction mixture was quenched with water and extracted (×3) with ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and evaporated to dryness. Residue was dissolved in MeOH (20 mL) and water (5 mL) and KOH (1.12 gr, 20 mmol) was added. The resulting solution was stirred at room temperature 24 hours, then solvents removed under reduced pressure. The residue was taken-up with AcOEt and KHSO4 5% solution. Aqueous phase was extracted with EtOAc several times. Collected organic phases were dried with Na2SO4, filtered and evaporated to dryness affording 600 mg of the title compound.

後処理

  1. additionwas added
  2. customReaction mixture
  3. customwas quenched with water
  4. extractionextracted (×3) with ethyl acetate
  5. dry with materialCollected organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. dissolutionResidue was dissolved in MeOH (20 mL)
  9. customsolvents removed under reduced pressure
  10. extractionAqueous phase was extracted with EtOAc several times
  11. dry with materialCollected organic phases were dried with Na2SO4
  12. filtrationfiltered
  13. customevaporated to dryness

出典と根拠

ORDレコード
ord-c74e290262b749e096a219d203999feb
出典データセット
uspto-grants-2015_08
特許番号
US09102662B2

関連ノート

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