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Phenylacetic Acid → 4-Hydroxy-4-(1-carboxy-1-phenyl-methyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1394437
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1394437
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Cl)(C)C.[C:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>C1COCC1>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][C:26]([OH:29])([CH:7]([C:8]([OH:10])=[O:9])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]
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Komponenten

5

Edukt 3

HCID 999Phenylacetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 670465474-Hydroxy-4-(1-carboxy-1-phenyl-methyl)piperidine-1-carboxylic acid tert-butyl esterAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of phenylacetic acid (13.7 g, 0.100 mol) in THF (90 mL) at 0° C. was slowly added iPrMgCl (2M in Et2O, 100 mL, 0.200 mol). The mixture was stirred at rt for 1 h and then N-Boc-4-piperidone (20.0 g, 0.100 mol) was added as a solid. Stirring was continued for 1 h and then the mixture was quenched with sat. NH4Cl and acidified to pH 2 using concentrated HCl. The mixture was extracted with EtOAc (×3) and the combined organic layers were dried over Na2SO4, filtered and concentrated to give the title compound (33.3 g, 99%) as a colorless foam which was of sufficient purity to continue to the next step:

Aufarbeitung

  1. customat 0° C.
  2. stirringStirring
  3. waitwas continued for 1 h
  4. customthe mixture was quenched with sat. NH4Cl
  5. extractionThe mixture was extracted with EtOAc (×3)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d5bf9a100a3c4de49884296febdb6d4e
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07348337B2

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