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Methyl 2-(bromomethyl)-4-methoxybenzoate → HCID 68509225, Verbindung

HRID 1715159
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1715159
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12]Br.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CO.C(N(CC)CC)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([N:28]2[CH2:12][C:5]3[C:4](=[CH:9][CH:8]=[C:7]([O:10][CH3:11])[CH:6]=3)[C:3]2=[O:14])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoateHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 68509225HCID 68509225, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-bromomethyl-4-methoxy-benzoic acid methyl ester (1.28 g, 4.94 mmol, 1.0 equiv) in methanol (9 mL) and triethylamine (0.83 mL) was added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.04 g, 5.19 mmol, 1.05 equiv; commercially available) and the reaction stirred at rt overnight. The reaction mixture was poured on crashed ice/diluted HCl, extracted with ethyl acetate, the combined organic phases washed with a sat. solution of NaHCO3 and water, dried over Na2SO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (3:7) yielding 0.84 g (49%) of the title compound as white crystals. MS (ISP): 347.3 [M+H]+.

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. extractionextracted with ethyl acetate
  3. washthe combined organic phases washed with a sat. solution of NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude material was purified with silica column chromatography
  7. washeluting with hexane/ethyl acetate (3:7)

Quellen und Nachweise

ORD-Eintrag
ord-e8e8e6ba52ef4662ba78840775cd762b
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799806B2

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