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Hexane → 2-Benzyl-6-(cis-3isopropyloxy-4-hydroxypyrrolidine1-yl)pyridine

HRID 1359369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1359369
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[CH2:17]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]2[CH2:34][C@H:33]3[O:35][C:36]([CH3:39])([CH3:38])[O:37][C@H:32]3[CH2:31]2)[N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:17]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N:30]2[CH2:31][C@H:32]([OH:37])[C@H:33]([O:35][CH:36]([CH3:39])[CH3:38])[CH2:34]2)[N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 697599182-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine

Produkt 1

HCID 697587042-Benzyl-6-(cis-3isopropyloxy-4-hydroxypyrrolidine1-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

A hexane solution containing 1.5 mol of diisobutylaluminum hydride was added little by little to a solution of 5.0 ml of diethyl ether containing 460 mg of 2-benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine at −20° C. After stirring at room temperature overnight, the reaction solution was poured into an aqueous ammonium chloride solution, and the mixture was filtered through Celite and extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to filtration through silica gel and eluted with ethyl acetate, to give 369 mg of the target compound.

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customthe solvent was removed
  5. filtrationThen, the residue was subjected to filtration through silica gel
  6. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-72f1f1c888a54251a8d13f89f3d8960d
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06599917B1

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