HCID 86620858, Verbindung → HCID 66687362, Verbindung

HRID 661539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661539
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:19][C:20]1[CH:21]=[C:22]([Mg]Br)[CH:23]=[CH:24][C:25]=1[Cl:26]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]([C:23]1[CH:22]=[CH:21][C:20]([Cl:19])=[C:25]([Cl:26])[CH:24]=1)[OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 86620858HCID 86620858, VerbindungHCID 178478192HCID 178478192, Verbindung

Produkt 1

HCID 66687362HCID 66687362, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.753 g, 2.95 mmol) in THF (12 mL) at 0° C. and under nitrogen was added 3,4-dichlorophenylmagnesium bromide (11.8 mL of a 0.5 M solution in pentanes, 5.9 mmol) dropwise over 10 minutes. After 20 minutes, the reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL) then extracted with EtOAc. The combined extracts were washed with brine then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (1.9 g). Purification by chromatography (silica, 5-20% EtOAc in hexanes) gave 2-butyl-2-[(3,4-dichloro-phenyl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.548 g, 1.36 mmol, 46%) as a colourless gum and as an inseparable mixture of diastereomers

Aufarbeitung

  1. customthe reaction mixture was quenched by the addition of saturated aqueous NH4Cl (30 mL)
  2. extractionthen extracted with EtOAc
  3. washThe combined extracts were washed with brine
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a yellow oil (1.9 g)
  7. customPurification by chromatography (silica, 5-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bc49f4b6a00e49a98515db3a6aabd6c5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084623B2

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