Sodium hydride → (3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazine

HRID 8481

Reaktionsgleichung

Reaktionsgleichung von HRID 8481
[H-].[Na+].F[C:4]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:5]=1[NH:6][C@@H:7]([CH3:10])[CH2:8][OH:9]>CN(C=O)C>[F:16][C:13]1[CH:12]=[CH:11][C:5]2[NH:6][C@@H:7]([CH3:10])[CH2:8][O:9][C:4]=2[C:14]=1[F:15]

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 11401466(2S)-2-(2,3,4-Trifluoroanilino)propanol

Produkt 1

HCID 11041424(3S)-3-Methyl-7,8-difluoro-2,3-dihydro-4H-1,4-benzoxazineAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To DMF (2 ml) was added sodium hydride (39 mg) and the mixture was heated to 60° C. in an oil bath. Next, a solution of the compound (100 mg) obtained in Example 51 in DMF was dropped therein to and the obtained mixture was stirred for 1 hour. After treating in a conventional manner, the mixture was subjected to silica gel column chromatography to give 60 mg (66%) of the title compound. The optical purity determined by HPCL was >94% ee. Various spectral data was identical with those of a specimen synthesized separately.

Aufarbeitung

  1. additionAfter treating in a conventional manner

Quellen und Nachweise

ORD-Eintrag
ord-db2c78a2be8b4889be10b76ac296dc5d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087778B2

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