Trimethylaluminum → Mglu1 C-11

HRID 2422717

Reaktionsgleichung

Reaktionsgleichung von HRID 2422717
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([CH3:18])=[C:16]([NH2:19])[S:15][N:14]=2)=[CH:9][CH:8]=1.[CH3:20][C@@H:21]1[CH2:23][C@H:22]1[C:24](OCC1C=CC=CC=1)=[O:25]>ClCCl>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:17]([CH3:18])=[C:16]([NH:19][C:24]([C@@H:22]3[CH2:23][C@H:21]3[CH3:20])=[O:25])[S:15][N:14]=2)=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 16682925TrimethylaluminumHCID 534010803-(4-Methoxyphenyl)-4-methylisothiazol-5-amineHCID 67180743HCID 67180743, Verbindung

Produkt 1

HCID 57404255Mglu1 C-11Ausbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Add trimethylaluminum (2 M in toluene, 3.59 g, 45.5 mmol) to a 0° C. solution of 3-(4-methoxyphenyl)-4-methylisothiazol-5-ylamine (10.0 g, 45.5 mmol) in dichloromethane (455 mL). Stir 5 min and add benzyl (R,R)-2-methylcyclopropane-carboxylate (8.64 g, 45.5 mmol). Heat to 50° C. with nitrogen flow to remove solvent. The resulting oil is heated at 50° C. for 3 h. Quench with water and dilute with EtOAc (300 mL). Wash with 0.1 N HCl, dry (K2CO3), evaporate, and crystallize from hexane/EtOAc to afford (R,R)—N-[3-(4-methoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide. Yield: 80.4%. ES-MS: m/e 303.0 (m+1). (The mother liquor may be used for further recrystallizations.)

Aufarbeitung

  1. customto remove solvent
  2. temperatureThe resulting oil is heated at 50° C. for 3 h
  3. customQuench with water
  4. additiondilute with EtOAc (300 mL)
  5. washWash with 0.1 N HCl
  6. dry with materialdry (K2CO3)
  7. customevaporate
  8. customcrystallize from hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b40c04fcb93d479c82f7717750b0d3ad
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960419B2

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