Water → (1S,3R,4R,6R)-4-Bromo-3,7,7-trimethylbicyclo[4.1.0]heptan-3-ol

HRID 2202715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202715
[CH:1]12[C:7]([CH3:9])([CH3:8])[CH:6]1[CH2:5][CH:4]=[C:3]([CH3:10])[CH2:2]2.C([O-])([O-])=O.[Ca+2].C1C(=O)N([Br:23])C(=O)C1.[OH2:24]>O1CCOCC1>[Br:23][C@@H:4]1[CH2:5][C@@H:6]2[C@@H:1]([C:7]2([CH3:9])[CH3:8])[CH2:2][C@@:3]1([CH3:10])[OH:24]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 10112Calcium CarbonateHCID 260493-CareneHCID 67184N-bromobutanimide

Produkt 1

HCID 13860085(1S,3R,4R,6R)-4-Bromo-3,7,7-trimethylbicyclo[4.1.0]heptan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of (+)-3-carene (4.09 g, 30 mmol), CaCO3 (3.90 g, 39 mmol) and NBS (6.94 g, 39 mmol) in water (15 mL) and 1,4-dioxane (30 mL) was stirred at room temperature for 1 h. The mixture was diluted with water (75 mL) and extracted with Et2O (100 mL). The organic layer washed with water (3×50 mL), saturated Na2S2O3 aq. (50 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silicagel chromatography (10% EtOAc/hexane as eluent) to provide compound C22-1 (4.53 g, 65%) as a white solid.

Aufarbeitung

  1. extractionextracted with Et2O (100 mL)
  2. washThe organic layer washed with water (3×50 mL), saturated Na2S2O3 aq. (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silicagel chromatography (10% EtOAc/hexane as eluent)
  6. customto provide compound C22-1 (4.53 g, 65%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-99bbb5849c374a1bb42b81590555298b
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365522B2

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