1,8-Diazabicyclo(5.4.0)undec-7-ene → ((1R,4S)-4-azidocyclopent-2-enyl)benzene

HRID 2404376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2404376
[C:1]1([C@@H:7]2[CH2:11][C@@H:10](O)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.O>[N:27]([C@H:10]1[CH2:11][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)=[N+:28]=[N-:29]

Komponenten

6

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 13613834(1R,4R)-4-phenylcyclopent-2-enol

Produkt 1

HCID 130951056((1R,4S)-4-azidocyclopent-2-enyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of Example 48A (458 mg, 2.86 mmol) and toluene (4.6 mL) was cooled to <5° C. and diphenylphosphoryl azide (0.740 mL, 3.43 mmol) and DBU (0.603 mL, 4.00 mmol) were added. After 5 hours at room temperature, LCMS showed complete reaction. Water (20 mL) and toluene (50 mL) were added and organic layer was washed with water (20 mL), 2N HCl (20 mL), and brine (10 mL) sequentially. The organic layer was dried (Na2SO4), filtered, and concentrated, and crude title compound was used in the next step. MS (DCI) m/z 203 (M+NH4)+.

Aufarbeitung

  1. customreaction
  2. washorganic layer was washed with water (20 mL), 2N HCl (20 mL), and brine (10 mL) sequentially
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-edc93e35cb4d42dba51d0a2d39640094
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802711B2

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