Imidazole → 4-Piperidineethanol TBS

HRID 79179

反応式

HRID 79179 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Si:14]([O:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 795ImidazoleHCID 11430Potassium Carbonate2 回HCID 28928tert-Butyldimethylsilyl chlorideHCID 739534-Piperidineethanol

生成物 1

HCID 162207594-Piperidineethanol TBS収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(piperidin-4-yl)ethanol (2.00 g, 15.5 mmol), t-butylchlorodimethylsilane (2.57 g, 17.0 mmol), and imidazole (1.05 g, 15.5 mmol) were taken up in dichloromethane (15 mL) and stirred for 22 hours. This solution was added to aqueous K2CO3 (80 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a pale yellow oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol) afforded a white solid. This solid was added to aqueous K2CO3 (60 mL) and extracted with dichloromethane+10% methanol (3×30 mL), the organics dried (MgSO4) and evaporated to give compound 292 as a yellow oil (3.24 g, 86%).

後処理

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a pale yellow oil
  5. washSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-10% methanol)
  6. customafforded a white solid
  7. extractionextracted with dichloromethane+10% methanol (3×30 mL)
  8. dry with materialthe organics dried (MgSO4)
  9. customevaporated

出典と根拠

ORDレコード
ord-823f08d8e54043b5ae2c31a6bb0c32cb
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

読み込み中…