1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-(Azidomethyl)quinoline

HRID 657770

Reaktionsgleichung

Reaktionsgleichung von HRID 657770
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11]O)[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1C=CC(OP(OC2C=CC=CC=2)([N:22]=[N+:23]=[N-:24])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(Cl)Cl>[N:22]([CH2:11][C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N:1]2)=[CH:6][CH:7]=1)=[N+:23]=[N-:24]

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 976097-QuinolinemethanolHCID 123414Diphenylphosphoryl azide

Produkt 1

HCID 598406937-(Azidomethyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of quinolin-7-ylmethanol (1.2 g, 7.2 mmol) and diphenylphosphonic azide (3.8 mL, 17 mmol) was dissolved in toluene (20 mL) and methylene chloride (6 mL). The mixture was cooled to 0° C. and neat 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL, 17 mmol) was added. The reaction was stirred for 30 minutes at 0° C. and then reacted at room temperature for 2 h. The mixture was diluted with CH2Cl2 (100 mL) and washed with water (100 mL×2). The organic layer was concentrated in vacuo and purified by silica gel chromatography (0-100% EtOAc/hexane) to afford a colorless oil.

Aufarbeitung

  1. customreacted at room temperature for 2 h
  2. washwashed with water (100 mL×2)
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified by silica gel chromatography (0-100% EtOAc/hexane)
  5. customto afford a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-be849a1188ac47cbb423c6b49b562b38
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076345B2

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