Aluminium lithium hydride → 3-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-

HRID 1891321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891321
C([O:3][C:4]([C:6]1([CH3:25])[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:18]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[C:6]([CH2:4][OH:3])([CH3:25])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 66653488HCID 66653488, Verbindung

Produkt 1

HCID 666532933-Pyrrolidinemethanol, 4-(4-chlorophenyl)-3-methyl-1-(phenylmethyl)-Ausbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid ethyl ester (5.75 g, 16.7 mmol) in THF (200 mL) at 0° C., was added portion wise LiAlH4 (381 mg, 10.0 mmol) over 20 minutes. After one hour at this temperature, the reaction mixture was carefully quenched by addition of icy water and then of an aqueous solution of NaHCO3. The product was extracted with EtOAc several times, the combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1) yielded the title product (4.0 g, 76%) as a colorless viscous oil. ES-MS m/e: 316.2 (M+H+).

Aufarbeitung

  1. customthe reaction mixture was carefully quenched by addition of icy water
  2. extractionThe product was extracted with EtOAc several times
  3. dry with materialthe combined organic phases were dried over NA2SO4 and purification by column chromatography (SiO2, EtOAc/H 1:4 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-33bc395525f94673a4c5ad776ea16a7b
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507535B2

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