Trimethylaluminum → (R,R)-N-[3-(3-fluoro-4-methoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide

HRID 2422712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422712
[CH3:1][C@@H:2]1[CH2:4][C@H:3]1[C:5](OCC1C=CC=CC=1)=[O:6].[F:15][C:16]1[CH:17]=[C:18]([C:24]2[CH:28]=[C:27]([NH2:29])[S:26][N:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C[Al](C)C>ClCCl.CCOC(C)=O.Cl.O>[F:15][C:16]1[CH:17]=[C:18]([C:24]2[CH:28]=[C:27]([NH:29][C:5]([C@@H:3]3[CH2:4][C@H:2]3[CH3:1])=[O:6])[S:26][N:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Komponenten

8

Edukt 3

HCID 16682925TrimethylaluminumHCID 67180743HCID 67180743, VerbindungHCID 671815313-(3-Fluoro-4-methoxyphenyl)isothiazol-5-ylamine

Produkt 1

HCID 67180639(R,R)-N-[3-(3-fluoro-4-methoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamideAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add benzyl (R,R)-2-methylcyclopropanecarboxylate (0.55 g, 2.89 mmol) to a 0° C. solution of 3-(3-fluoro-4-methoxyphenyl)isothiazol-5-ylamine (0.59 g, 2.63 mmol) and trimethylaluminum (2.0 M in toluene, 5.26 mmol) in dichloromethane (5 mL) and allow reaction to naturally warm to room temperature. Warm the reaction mixture to 40° C. and allow to stir overnight. Dilute the reaction mixture with EtOAc (100 mL) and 1 N HCl (40 mL) and water (100 mL), collect the organic phase, and evaporate. Chromatography over silica gel eluting with 25-50% EtOAc in hexane affords (R,R)—N-[3-(3-fluoro-4-methoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide. Yield: 55.9%. ES-MS: m/e 307.0 (m+1).

Aufarbeitung

  1. customreaction
  2. temperatureWarm the reaction mixture to 40° C.
  3. customcollect the organic phase
  4. customevaporate

Quellen und Nachweise

ORD-Eintrag
ord-01de0d1aa4eb42cab0a9171a09706d32
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960419B2

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