Ethyl diazoacetate → Ethyl 2-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]cyclopropanecarboxylate

HRID 1451529

Reaktionsgleichung

[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]=[CH2:19])=[C:8]2[CH3:20])=[CH:4][CH:3]=1.[N+](=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N-]>C1(C)C=CC=CC=1.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:18]3[CH2:19][CH:25]3[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:8]2[CH3:20])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a room temperature solution of the indole from Step 1 (3.91 g, 11.0 mmol) in 20 mL toluene was added rhodium (II) octanoate dimer (109 mg, 0.14 mmol), and the solution was cooled to 0° C. A solution of ethyl diazoacetate (3.0 mL, 28.5 mmol) in 13 mL toluene was then added via syringe pump at 1.2 mL/hr. Fresh catalyst was then added along with an additional 1 mL ethyl diazoacetate in toluene over 2.5 h. The crude reaction mixture was applied directly to a silica gel column and eluted with 1% to 2.5% ethyl acetate/toluene. 1.1 g of the trans isomer of the title compound was thus obtained, followed by 1.2 g of the cis isomer of the title compound.

Aufarbeitung

customThe crude reaction mixture
washeluted with 1% to 2.5% ethyl acetate/toluene

Quellen und Nachweise

ORD-Eintrag: ord-ee257a9407da4a4ea70b259c601b9e2e
Quelldatensatz: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05604253

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