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

HRID 866565Notes

Reaction equation

HRID 866565 reaction equation
[C-:1]#[N:2].[K+].[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]>CN(C)P(=O)(N(C)C)N(C)C>[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 9032Potassium CyanideHCID 12881134Methyl 2-oxobicyclo[3.1.0]hexane-1-carboxylate

Product 1

HCID 24977136Methyl 2-(cyanomethyl)-5-oxocyclopentane-1-carboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In argon atmosphere, potassium cyanide (260 mg, 4 mmol) and 2-oxo-bicyclo [3.1.0] hexane-1-carboxylic acid methyl ester (462 mg, 3 mmol) were added to hexamethylphosphoric triamide (3 ml). The mixture was stirred at the room temperature for 24 hours and was treated in accordance with the process of Preparation 4 to obtain 300 mg of 5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester. Yield: 55%.

Workup

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

Sources & evidence

ORD record
ord-3e5d58cfe1e1479ab5a4ef733eacd26a
Source dataset
uspto-grants-1978_07
Patent number
US04100184

Reaction notes

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