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

HRID 1918683Notes

Reaction equation

HRID 1918683 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 668319813-benzyl-N-(2-(5-chloro-1H-indol-3-yl)ethyl)pyrrolidine-1-carboxamideYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-07c740aafa854e5bb354d420cba3f672
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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