Sodium Cyanide → Methyl 2-(cyanomethyl)-5-oxocyclopentane-1-carboxylate

HRID 866564Notes

Reaction equation

HRID 866564 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6]([C:8]12[CH2:13][CH:12]1[CH2:11][CH2:10][C:9]2=[O:14])=[O:7]>CS(C)=O>[CH3:4][O:5][C:6]([CH:8]1[CH:12]([CH2:13][C:1]#[N:2])[CH2:11][CH2:10][C:9]1=[O:14])=[O:7]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 12881134Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate

Product 1

HCID 24977136Methyl 2-(cyanomethyl)-5-oxocyclopentane-1-carboxylateYield 60.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In argon atmosphere, sodium cyanide (200 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to dimethyl sulfoxide (2ml). The mixture was stirred at the room temperature for one night and was treated in accordance with the process of Preparation 4 to obtain 328 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 60%.

Workup

  1. additionwas treated in accordance with the process of Preparation 4

Sources & evidence

ORD record
ord-c6d006e422dc4ab09581c0986427578d
Source dataset
uspto-grants-1978_07
Patent number
US04100184

Reaction notes

Loading…