Reaktion #687047

Reaktionsgleichung

1-Benzyl-3-(4-nitro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

benzylamine

1-nitro-4-(2-nitro-vinyl)-benzene

→

desired compound

1-Benzyl-3-(4-nitro-phenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITION0.70 g of silica gel (SiO2) was added
2. 2
   workup.STIRRINGAfter stirring at RT for 8 h
3. 3
   workup.STIRRINGthe mixture was stirred for 14 h at RT
4. 4
   FiltrationThe mixture was then filtered through diatomaceous earth
5. 5
   Einengenthe filtrate was concentrated in vacuo

Vorschrift

1-Benzyl-3-(4-nitro-phenyl)-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester. To a stirred solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.69 g) in toluene (5 mL) was added 378 μL of benzylamine. The mixture was stirred for 10 min and then 0.70 g of silica gel (SiO2) was added. After stirring at RT for 8 h, 0.77 g of 1-nitro-4-(2-nitro-vinyl)-benzene in toluene (5 mL) was added and the mixture was stirred for 14 h at RT. The mixture was then filtered through diatomaceous earth and the filtrate was concentrated in vacuo. Chromatography on SiO2 (8 to 20% EtOAc/hexanes) afforded 0.48 g of the desired compound. MS (ESI): exact mass calculated for C25H27N3O4, 433.20. found, m/z 434.2 [M+H]+, 456.2 [M+Na]+.

Quelle