Ammonium formate → HCID 19050034, Verbindung

HRID 1780221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780221
C([O:8][C:9]1[CH:10]=[C:11]2[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH:26]([CH2:36][Cl:37])[C:12]2=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]2[C:22]([O:24][CH3:25])=[O:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[Pd]>[CH3:25][O:24][C:22]([C:14]1[C:13]2[C:17](=[C:9]([OH:8])[CH:10]=[C:11]3[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:27][CH:26]([CH2:36][Cl:37])[C:12]3=2)[NH:16][C:15]=1[C:18]([F:21])([F:20])[F:19])=[O:23]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 19050108Benzo[1,2-b:4,3-b′]dipyrrole-1,6(3H)-dicarboxylic acid, 8-(chloromethyl)-7,8-dihydro-4-(phenylmethoxy)-2-(trifluoromethyl)-, 6-(1,1-dimethylethyl) 1-methyl ester

Produkt 1

HCID 19050034HCID 19050034, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 2.63 ml of tetrahydrofuran, was dissolved 106.7 mg (198 μmol) of methyl 5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate. Thereto, 64 mg of 10% palladium on carbon was added, and then 656.4 μl of 25% ammonium formate was added dropwise under ice cooling. The mixture was stirred for one hour, and then the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain methyl-3-t-butoxycarbonyl-1-chloromethyl-5-hydroxy-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate in a yield of 87.9 mg (99%).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-04ba2c60962d4c158fd19f2d89d8f437
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629430

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