Sodium hydride → (+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one

HRID 1363354

Reaktionsgleichung

Reaktionsgleichung von HRID 1363354
[OH:1][C:2]1[C:7]([C@@H:8]2[CH2:12][CH2:11][N:10]([CH3:13])[C@H:9]2[CH2:14][OH:15])=[C:6]([O:16][CH3:17])[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[C:20](=[O:22])[CH3:21].[F:23][C:24]([F:36])([F:35])[C:25]1[CH:34]=[CH:33][C:28]([C:29](OC)=O)=[CH:27][CH:26]=1.[H-].[Na+]>CN(C=O)C>[OH:15][CH2:14][C@H:9]1[C@H:8]([C:7]2[C:6]([O:16][CH3:17])=[CH:5][C:4]([O:18][CH3:19])=[C:3]3[C:2]=2[O:1][C:29]([C:28]2[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:35])[F:36])=[CH:34][CH:33]=2)=[CH:21][C:20]3=[O:22])[CH2:12][CH2:11][N:10]1[CH3:13]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 520447Methyl 4-(trifluoromethyl)benzoateHCID 59318484(-)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanone

Produkt 1

HCID 66933632(+)-trans-8-(2-Hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-2-(4-trifluoromethyl-phenyl)-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound of example 6 (1.5 g, 4.84 mmol) in dry DMF (15 mL) was reacted with methyl 4-trifluoromethylbenzoate (3.27 g, 16.02 mmol) in the presence of NaH (50%, 1.2 g, 25 mmol) as described in example 16, to obtain the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-910d8171c19b4586b97e24f691c06dc4
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884127B2

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