Hydrochloric Acid → 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 501298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501298
Cl.[OH-:2].[NH4+:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl>N1C=CC=CC=1>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=[N:3][OH:2])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 13908798HCID 13908798, VerbindungHCID 588177114-[1-(3-Bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 724345734-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl EsterAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Add ammonium hydroxide hydrochloride (50.68 mmol, 3.52 g, 2.00 equivalents) to a stirred solution of 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester (25.54 mol, 9.84 g, 1.00 equivalents) in pyridine (47.5 mL). Stir at room temperature overnight and at 70° C. for 4 hours. Cool the reaction mixture and add hydrochloric acid (3 M solution, 115 mL). Extract the reaction mixture with dichloromethane (115 mL), filter the organic layer, wash with water (100 mL), dry over magnesium sulfate, filter and evaporate. Recrystallize the resulting residue from toluene to yield a white solid (4.84 g).

Aufarbeitung

  1. temperatureCool the reaction mixture
  2. extractionExtract the reaction mixture with dichloromethane (115 mL)
  3. filtrationfilter the organic layer
  4. washwash with water (100 mL)
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate
  8. customRecrystallize the resulting residue from toluene

Quellen und Nachweise

ORD-Eintrag
ord-cb0d64277af14f2caca8e5826e37ce6e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772252B2

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