3-Acetylindole → tert-Butyl 3-acetyl-1H-indole-1-carboxylate

HRID 583779

Reaktionsgleichung

Reaktionsgleichung von HRID 583779
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>C1COCC1>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:13])[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 128023-AcetylindoleHCID 90495Di-tert-butyl dicarbonate

Produkt 1

HCID 14593498tert-Butyl 3-acetyl-1H-indole-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-acetylindole (0.01 mol) in THF is added (BOC)2O (0.01 mol) and a tertiary amine base (0.01 mol), and the mixture is stirred. Reaction progress may be followed by TLC or HPLC. When a sufficient amount of desired product is formed, the mixture (or, optionally, the residue which is obtained after first rotary evaporating off the reaction solvent) is partitioned between ethyl acetate and an excess of about 0.1 M sodium hydroxide. The organic layer is washed with brine, dried over sodium sulfate, and rotary evaporated to give 3-acetyl-1-(tert-butoxycarbonyl)-indole, which may be purified, if needed or desired, by chromatography on silica gel or crystallization.

Aufarbeitung

  1. customReaction progress

Quellen und Nachweise

ORD-Eintrag
ord-03702e6931274fa9b08f397e5b399321
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924276B2

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