Ethyl cyanoformate → Ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylate

HRID 1943161Notes

Reaction equation

HRID 1943161 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][C:6]#[CH:7].[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:9]>>[CH:7]1[C:6]2[CH2:5][CH2:4][CH2:3][C:2]=2[CH:1]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1

Participants

3

Reactant 2

HCID 69336Ethyl cyanoformateHCID 3371211,6-Heptadiyne

Product 1

HCID 14735905Ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylateYield 21%

Procedure

A solution of 1,6-heptadiyne (1.242 ml, 10.85 mmol) and ethyl cyanoformate (1.063 ml, 10.85 mmol) in dry degassed 1,4-dioxane (100 ml) under argon at rt was treated with cyclopentadienyl-Cobalt(I)-dicarbonyl (0.293 g, 1.628 mmol) and then heated at reflux for 18 h. Reaction was then evaporated, treated with toluene (100 ml), re-evaporated, dissolved in DCM (100 ml), filtered through a short pad of Kieselguhr, eluting with DCM, organic extracts evaporated, chromatographed (0-100% DCM:40-60 Petroleum ether then 0-10% methanol/DCM) to give product as an impure brown oil (427 mg, 21%).

Workup

  1. customdegassed 1,4-dioxane (100 ml) under argon at rt
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customReaction
  5. customwas then evaporated
  6. additiontreated with toluene (100 ml)
  7. customre-evaporated
  8. dissolutiondissolved in DCM (100 ml)
  9. filtrationfiltered through a short pad of Kieselguhr
  10. washeluting with DCM, organic extracts
  11. customevaporated
  12. customchromatographed (0-100% DCM

Sources & evidence

ORD record
ord-eee904e406cf47e489af201e658cd432
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

Loading…