1,8-Diazabicyclo(5.4.0)undec-7-ene → 4(R)-Azido-6,8-dibromo-chroman

HRID 1008959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1008959
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C@@H:5]2O.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1.C(OC(=O)C)C>[N:28]([C@H:5]1[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][CH2:7][CH2:6]1)=[N+:29]=[N-:30]

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67304261(S)-6,8-Dibromochroman-4-ol

Produkt 1

HCID 866200164(R)-Azido-6,8-dibromo-chroman

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution containing 6,8-dibromo-chroman-4(S)-ol in tetrahydrofuran (0.17M) and 1.2 equivalents of diphenylphosphorylazide was stirred for 15 minutes at room temperature. The solution was cooled to 10° C. and 2.5 equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene added. The mixture was stirred with gradual warming to room temperature and maintained for 48 h. The mixture was diluted with ethylacetate and washed with brine followed by water. The organic phase was concentrated to afford the title compound as a tan oil.

Aufarbeitung

  1. temperatureThe solution was cooled to 10° C.
  2. stirringThe mixture was stirred
  3. temperaturewith gradual warming to room temperature
  4. temperaturemaintained for 48 h
  5. washwashed with brine
  6. concentrationThe organic phase was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7dbc9ef49184c28889d6fa51a957303
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973050B2

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