1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 1431990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431990
O[C@H:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=[O:13])[CH:5]=[CH:4][C:3]1=2.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([C@@H:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=[O:13])[CH:5]=[CH:4][C:3]1=2)=[N+:29]=[N-:30]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 59771799(S)-5-hydroxy-5,6,7,8-tetrahydronapthalene-2-carbaldehyde

Produkt 1

HCID 59771822(R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-5-Hydroxy-5,6,7,8-tetrahydronapthalene-2-carbaldehyde (19.73 mmol) was dissolved in 50 mL of toluene and cooled to 0° C. Diphenylphosphoryl azide (29.6 mmol, 1.5 eq) was added, followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (23.07 mmol, 1.2eq). After stirring at room temperature overnight, the solvent was evaporated. The residue was purified by SiO2 chromatography (5-30% ethyl acetate in dichloromethane) to afford the title compound. MS (m/z): 204.2 (M+H).

Aufarbeitung

  1. customthe solvent was evaporated
  2. customThe residue was purified by SiO2 chromatography (5-30% ethyl acetate in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3182dd554647409aac6941f83c79fe94
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612060B2

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