Imidazole → 4-Piperidineethanol TBS

HRID 79179

반응식

HRID 79179 반응식
[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]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 11430Potassium Carbonate2회HCID 28928tert-Butyldimethylsilyl chlorideHCID 739534-Piperidineethanol

생성물 1

HCID 162207594-Piperidineethanol TBS수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-823f08d8e54043b5ae2c31a6bb0c32cb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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