Dimethylformamide → 3-(4-Chlorocarbonylbicyclo[2.2.2]oct-1-yl)propionic acid methyl ester

HRID 2105698Notes

Reaction equation

HRID 2105698 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].CN(C=O)C.[CH3:12][O:13][C:14]([CH2:16][CH2:17][C:18]12[CH2:25][CH2:24]C(C(O)=O)([CH2:22][CH2:23]1)[CH2:20][CH2:19]2)=[O:15]>C(Cl)Cl>[CH3:12][O:13][C:14](=[O:15])[CH2:16][CH2:17][C:18]12[CH2:23][CH2:22][C:1]([C:2]([Cl:4])=[O:3])([CH2:24][CH2:25]1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 166564244-(2-Methoxycarbonylethyl)bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 866089723-(4-Chlorocarbonylbicyclo[2.2.2]oct-1-yl)propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (794 mg, 6.25° mmol) in methylene chloride (5 ml) plus a drop of DMF is slowly added to a mixture of 4-(2-Methoxycarbonylethyl)-bicyclo[2.2.2]octane 1-carboxylic acid (XXI, Example 96, 1.2 g, 5 mmol) in methylene chloride (20 ml). The reaction mixture is stirred for 2 hr and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ3.66, 2.29, 1.95, 1.54 and 1.46.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-7283f0794aaa4cd99a7e92983ee4c03d
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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