1,8-Diazabicyclo(5.4.0)undec-7-ene → (4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

HRID 1009164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009164
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:6][C@H:5]2O.C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O>[N:32]([C@@H:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[O:8][C:7]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:6]1)=[N+:33]=[N-:34]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67305384(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

Produkt 1

HCID 86614139(4S)-4-azido-6-bromo-2-methyl-2-(trifluoromethyl)chroman

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a cooled (ice bath) solution of (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol (277 mg, 890 μmol) was added drop wise diphenylphosphoryl azide (249 μl, 1158 μmol). After stirring 20 min, 1,8-diazabicyclo(5.4.0)undec-7-ene (173 μl, 1158 μmol) was added drop wise. The reaction was stirred at the same temperature for 2 h, then stirred 15 h at ambient temperature. Water was added to quench the reaction. The resulted mixture was extracted with EtOAc. The organics were washed with brine, dried over Na2 SO4, filtered and concentrated. The residue was purified on a silica gel column (5-20% EtOAc/hexane) to afford the title compound. MS m/z: 308 (M−N2).

Aufarbeitung

  1. stirringThe reaction was stirred at the same temperature for 2 h
  2. stirringstirred 15 h at ambient temperature
  3. customto quench
  4. customthe reaction
  5. extractionThe resulted mixture was extracted with EtOAc
  6. washThe organics were washed with brine
  7. customdried over Na2 SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on a silica gel column (5-20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7634df07b3794ed68e474b05170d61e8
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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