Sodium hydride → 5-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid methyl ester

HRID 2281618Notes

Reaction equation

HRID 2281618 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[NH:7][CH2:6]1)=[O:4].[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([CH2:14][CH2:15][CH2:16][N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5571191-(3-Bromopropyl)pyrroleHCID 131181175-Oxo-pyrrolidine-3-carboxylic acid methyl ester

Product 1

HCID 671207165-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Oxo-pyrrolidine-3-carboxylic acid methyl ester (1 eq.) in dry DMF is added NaH (1.1 eq.) followed by 1-(3-bromo-propyl)-1H-pyrrole (1 eq.). The reaction mixture is stirred at room temperature overnight. Purification is by normal phase chromatography to yield 5-Oxo-1-(3-pyrrol-1-yl-propyl)-pyrrolidine-3-carboxylic acid methyl ester.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-2712d79211654c6cac3fdc7d2628ed00
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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