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

HRID 58693Notes

Reaction equation

HRID 58693 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-f67107a9b64c4c68826776efa0c3713b
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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