Sodium Iodide → Tert-butyl 1-cyanocyclobutane-1-carboxylate

HRID 2170106Notes

Reaction equation

HRID 2170106 reaction equation
[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].Br[CH2:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>C(C(C)=O)C>[C:7]([O:6][C:4]([C:3]1([C:1]#[N:2])[CH2:14][CH2:13][CH2:12]1)=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 70693tert-Butyl cyanoacetate

Product 1

HCID 66797886Tert-butyl 1-cyanocyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl 2-cyanoacetate (4.0 g, 28.3 mmol), 1,3-dibromopropane (6.29 g, 31.2 mmol) in methyl ethyl ketone (100 ml) was treated with potassium carbonate (11.75 g, 85 mmol). The reaction mixture was heated to 80° C. for 17 h and then NaI (catalyst) (0.21 g, 1.42 mmol) was added. The mixture was heated at 80° C. for 6 days and then allowed to cool to RT. The mixture was filtered through Celite® (filter material) and the filtrate was concentrated in vacuo. Purification by chromatography on silica eluting with 10% EtOAc in iso-hexane afforded the title product as a colourless oil; 1H NMR (400 MHz, CDCl3) δ 2.64 (4H, m), 2.22 (2H, m), 1.53 (9H, s).

Workup

  1. temperatureThe mixture was heated at 80° C. for 6 days
  2. temperatureto cool to RT
  3. filtrationThe mixture was filtered through Celite® (filter material)
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification by chromatography on silica eluting with 10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-de5b8111eaf34467acd8424d00ab8c06
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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