Sodium hydride → HCID 67016478, Verbindung

HRID 1891322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891322
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([CH2:21][OH:22])([CH3:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1>CN(C=O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:10]([CH2:21][O:22][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)([CH3:20])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 8170982-Bromo-5-chloropyridineHCID 666532933-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-

Produkt 1

HCID 67016478HCID 67016478, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of [(3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidin-3-yl]-methanol (4.0 g, 12.7 mmol) in DMF (60 mL) at RT was added NaH (608 mg, 60%, 15.2 mmol). The reaction mixture was heated at 50° C. for 30 minutes, then cooled down to RT before 2-bromo-5-chloropyridine (3.66 g, 19.0 mmol) was added. The resulting brownish solution was stirred overnight at 60° C., then concentrated under high vacuum. The residues was taken up in EtOAc, and washed with water. The organic phase was dried over Na2SO4 and a purification by column chromatography gave 3.90 g (72%) of the title product as a viscous oil. ES-MS m/e: 427.2 (M+H+).

Aufarbeitung

  1. additionwas added
  2. concentrationconcentrated under high vacuum
  3. washwashed with water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customa purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04da5e10f9274a75beb7cfd6600507c3
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507535B2

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