Water → HCID 66797877, Verbindung

HRID 1677935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677935
[O:1]=[C:2]1[C@H:7]2[CH2:8][C@H:4]([CH:5]=[CH:6]2)[N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH2:16].C[N+]1([O-])CC[O:21]CC1.S(=O)(O)[O-].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:16][C@H:6]1[C@@H:5]([OH:21])[C@H:4]2[CH2:8][C@@H:7]1[C:2](=[O:1])[N:3]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Komponenten

7

Edukt 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 11830665(1R,4S)-tert-Butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 66797877HCID 66797877, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate (500. mg, 2.39 mmol) in acetone (20.0 mL) was added a 4% aqueous solution of osmium tetroxide in H2O (0.015 mL, 0.00239 mmol). To the resulting mixture was added a 10.2 M aqueous solution of N-methylmorpholine N-oxide (0.262 mL, 2.67 mmol) dropwise over 1 h. At this point, a 0.240 M solution of aqueous sodium bisulfite (1.00 mL, 0.240 mmol) was added, the mixture was filtered through celite and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 20 to 70% EtOAc in DCM to afford the title compound (420. mg, 72%). LC/MS: Rt=0.94 min, ES+ 244 (FA standard).

Aufarbeitung

  1. filtrationthe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via silica gel chromatography
  4. washeluting with a gradient of 20 to 70% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-394c26534c54441b8c57a4f461fcf25a
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008307B2

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