Methanamine, N-methoxy-, hydrochloride (1:1) → trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide

HRID 475059

Reaktionsgleichung

Reaktionsgleichung von HRID 475059
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:14][O:15][NH:16][CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:14][O:15][N:16]([CH3:17])[C:10]([C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12]

Komponenten

7

Edukt 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 15141060trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of 35 (117.5 g, 724.48 mmol, 1.00 equiv) in DMF (1.2 L) under N2 was added methoxy(methyl)amine hydrochloride (82.3 g, 844.10 mmol, 1.17 equiv), HATU (329 g, 775.58 mmol, 1.07 equiv), and DIPEA (117.5 mL). The reaction mixture was stirred under N2 at 25° C. overnight and then diluted with water (700 mL). The organic phase was extracted with EtOAc (3×1 L), and the combined organic layers were washed with water (3×1 L) and brine (1×1 L), dried (Na2SO4), filtered and concentrated in vacuo. The residue purified by SiO2 chromatography and eluted with EtOAc/petroleum ether (10 to 50% EtOAc) to afford 62.5 g (42%) of trans-N-methoxy-N-methyl-2-phenylcyclopropane-1-carboxamide (37) as a light yellow oil.

Aufarbeitung

  1. extractionThe organic phase was extracted with EtOAc (3×1 L)
  2. washthe combined organic layers were washed with water (3×1 L) and brine (1×1 L)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue purified by SiO2 chromatography
  7. washeluted with EtOAc/petroleum ether (10 to 50% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-117500c628e149d69f42b203e2b8eb9b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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