Hydrochloric Acid → Racemic 4-(2-formyl-4-iodo-phenoxy)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

HRID 1095178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095178
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH:22]2[CH:20]([O:21]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>CN(C=O)C.[K]>[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH:22]([O:1][C:2]2[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=2[CH:4]=[O:5])[CH:20]([OH:21])[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2526125-IodosalicylaldehydeHCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Produkt 1

HCID 87086948Racemic 4-(2-formyl-4-iodo-phenoxy)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 5462222PotassiumLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 2-hydroxy-5-iodo-benzaldehyde (Aldrich, 4.96 g, 20 mmol) in DMF (80 mL), potassium carbobate (10 g, 60 mmol) and 7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (8 g, 40 mmol) were added and the mixture was stirred at 70° C. for three days and 80° C. for two days. The mixture was poured into 1N HCl and the mixture was extracted with EtOAc (3×50 mL). The extracts were combined and dried over sodium sulfate and concentrated to give an oil, which was chromatographied on an ISCO machine (10-30% EtOAc/Hexanes) to yield an oil, 3.4 g. MS (H+), 348.

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (3×50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto give an oil, which
  5. customto yield an oil, 3.4 g

Quellen und Nachweise

ORD-Eintrag
ord-be7da1fa88b441deb3a345feb1848cd5
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134001B2

Notizen zur Reaktion

Wird geladen…