Sodium hydride → 3-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyrrolidine-1-carboxamide

HRID 58693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58693
[H-].[Na+].[CH2:3]([CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][CH2:26][NH:27][C:28](=O)[O:29]C1C=CC=CC=1>C1COCC1>[CH2:3]([CH:10]1[CH2:14][CH2:13][N:12]([C:28]([NH:27][CH2:26][CH2:25][C:19]2[C:18]3[C:22](=[CH:23][CH:24]=[C:16]([Cl:15])[CH:17]=3)[NH:21][CH:20]=2)=[O:29])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 38297913-BenzylpyrrolidineHCID 66831882phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate

Produkt 1

HCID 668319813-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyrrolidine-1-carboxamideAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

NaH in mineral oil (60%) (12.20 mg) was added to a mixture of 3-benzylpyrrolidine (0.085 g; 0.508 mmol) in THF (2 mL) and stirred at room temperature for 10 minutes. Phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate (0.080 g; 0.245 mmol) in THF (2 mL) was added to the above mixture and stirred at room temperature overnight. The crude material was purified by preparative HPLC (method 2) to yield 0.03 g (31%) of 3-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyrrolidine-1-carboxamide as a white solid.

Aufarbeitung

  1. stirringstirred at room temperature overnight
  2. customThe crude material was purified by preparative HPLC (method 2)

Quellen und Nachweise

ORD-Eintrag
ord-f67107a9b64c4c68826776efa0c3713b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

Notizen zur Reaktion

Wird geladen…