Iodoethane → 1-(4-Bromo-benzyl)-2-ethoxymethyl-pyrrolidine

HRID 2236508Notes

Reaction equation

HRID 2236508 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[CH2:12][OH:13])=[CH:4][CH:3]=1.[CH2:16](I)[CH3:17].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[CH2:12][O:13][CH2:16][CH3:17])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 44827912(1-(4-Bromobenzyl)pyrrolidin-2-yl)methanol

Product 1

HCID 686929221-(4-Bromo-benzyl)-2-ethoxymethyl-pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[1-(4-Bromo-benzyl)-pyrrolidin-2-yl]-methanol (269 mg, 1.0 mmol) and EtI (234 mg, 1.5 mmol) is mixed at 0° C. in DMF (DMF) (10 mL). To this mixture is then added NaH (60 mg, 60% suspension in mineral oil, 1.5 mmol). The resulting mixture is stirred at room temperature for 1 h before aqueous workup. The resulting residue is directly used in the next step.

Sources & evidence

ORD record
ord-abbdf561bc5a4c39a4ab45cb92ab78b2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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