2,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide → (S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 501706

Reaktionsgleichung

Reaktionsgleichung von HRID 501706
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]([F:30])([F:29])[C:14]([NH:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[C@H:19]([OH:28])[CH2:18]1)=[O:15]>C(Cl)Cl>[F:12][C:13]([F:29])([F:30])[C:14]([NH:16][C@@H:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[C:19](=[O:28])[CH2:18]1)=[O:15]

Komponenten

4

Edukt 2

HCID 596761532,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamideHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 1472787(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Step AF (1): Pyridinium chlorochromate (362 mg) was added to a stirred suspension of 4Ao MS and 2,2,2-trifluoro-N-((1S,3R)-3-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide (200 mg) from Step T (1) in DCM (6 mL) at rt. The resulting mixture was stirred for 2 h. The reaction mixture was filtered through a pad of Celite, and the filtrate was evaporated in vacuo to give (S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide. This crude product was carried forward without purification. 1H NMR (400 MHz, CD3OD) δ ppm 2.56 (m, 1H) 3.08 (m, 1H) 3.83 (s, 3H) 5.58 (m, 1H) 6.96 (m, 2H) 7.29 (m, 1H) 7.62 (s, 1H). Optical rotation [α]D=−124.16 (c=6.84 mg/mL, methanol).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a3b6a2f22e9a4425a90e56acb71b6ef1
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772221B2

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