Imidazole → 4-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine

HRID 79173

反応式

HRID 79173 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[C:9]([Si:13](Cl)([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10].N1C=CN=C1.C([O-])(O)=O.[Na+].[OH-].[Na+]>ClCCl>[Si:13]([O:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:15])[CH3:14]

参加物

7

反応物 5

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 4207714-PiperidinemethanolHCID 516892Sodium Bicarbonate

生成物 1

HCID 670219944-{[(Tert-butyldimethylsilyl)oxy]methyl}piperidine収率 95.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Piperidin-4-ylmethanol (2.50 g, 21.7 mmol), t-butylchlorodimethylsilane (4.13 g, 23.9 mmol), and imidazole (1.48 g, 21.7 mmol) were dissolved in dichloromethane (25 mL) and stirred at room temperature for 18 hours. The reaction was added to aqueous NaHCO3 (200 mL, 50% saturated) and extracted with dichloromethane (3×150 mL). The combined organics were dried (MgSO4) and evaporated to give a yellow oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol) gave a soft white solid, which was then added to 0.5 M NaOH (100 mL) and extracted with dichloromethane+10% methanol (3×100 mL). The combined organics were dried (MgSO4) and evaporated to give compound 284 as a pale yellow oil (4.75 g).

後処理

  1. extractionextracted with dichloromethane (3×150 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil
  5. washSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol)
  6. customgave a soft white solid, which
  7. extractionextracted with dichloromethane+10% methanol (3×100 mL)
  8. dry with materialThe combined organics were dried (MgSO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-065dcabb5fa64dfe8716560e51088083
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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