Oxalyl chloride → 1-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-carbonyl chloride

HRID 30258Notes

Reaction equation

HRID 30258 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[S:14][CH:15]=[C:16]([Br:18])[CH:17]=2)[CH:10]([C:19]([OH:21])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[S:14][CH:15]=[C:16]([Br:18])[CH:17]=2)[CH:10]([C:19]([Cl:25])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 67206869HCID 67206869, compound

Product 1

HCID 862291871-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from step c) (4.6 g, 12.6 mmol) in CH2Cl2 (63 ml) was treated with DMF (3-5 drops) and oxalyl chloride (2.4 g, 18.9 mmol) for 2 hours. Next, the solvent was evaporated in vacuo to give 4.04 g (100%) of the subtitle compound that was used without further purification.

Workup

  1. customNext, the solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f62d7a9f220f47d0a980772f9f1b0335
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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