1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18401884, Verbindung

HRID 1018663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018663
C1(COC2C=CC3C(O)CCCCC=3C=2)CCCCC1.C1CCN2C(=NCCC2)CC1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51].C1(COC2C=CC3C=CCCCC=3C=2)CCCCC1>C1(C)C=CC=CC=1.CCOC(C)=O>[N:49]([CH:52]1[C:58]2[CH:59]=[CH:60][C:61]([O:63][CH2:64][CH:65]3[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]3)=[CH:62][C:57]=2[CH2:56][CH2:55][CH2:54][CH2:53]1)=[N+:50]=[N-:51]

Komponenten

7

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 18401893HCID 18401893, VerbindungHCID 86585965HCID 86585965, Verbindung

Produkt 1

HCID 18401884HCID 18401884, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (14.2 g, 52.0 mmol) in toluene (100 mL) at 0° C. was added DBU (9.4 mL, 62.9 mmol) followed by diphenylphosphoryl azide (13.6 mL, 62.9 mmol). The mixture was allowed to stir for 18 h at rt, diluted with EtOAc, then washed successively with 1 N HCl, and water. The organic layer was dried over MgSO4, filtered, concentrated, and chomatographed over silica gel (5% EtOAc/hexane) to yield a 7:3 mixture of 5-azido-2-cyclohexylmethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene/3-cyclohexylmethoxy-6,7-dihydro-5H-benzocycloheptene (12.6 g). This mixture was used without further purification in the next reaction.

Aufarbeitung

  1. washwashed successively with 1 N HCl, and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield
  6. customThis mixture was used without further purification in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-65094fee4916495485170592acd0d099
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06482852B2

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