Ethyl cyanoformate → Ethyl 5,6,7,8-tetrahydro-3-isoquinolinecarboxylate

HRID 1943157

Reaction equation

HRID 1943157 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:10]>>[CH:8]1[C:7]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[CH:1]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=1

Participants

3

Reactant 2

HCID 69336Ethyl cyanoformateHCID 700991,7-Octadiyne

Product 1

HCID 12384001Ethyl 5,6,7,8-tetrahydro-3-isoquinolinecarboxylateYield 21%

Procedure

A solution of 1,7-octadiyne (4.00 ml, 30.1 mmol) and ethyl cyanoformate (2.95 ml, 30.1 mmol) in dry degassed 1,4-dioxane (500 ml) under argon at rt was treated with cyclopentadienyl-Cobalt(I)-dicarbonyl (0.814 g, 4.52 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 (1.27 g, 21%).

Workup

  1. customdegassed 1,4-dioxane (500 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-f57b8a48b6f84075b17b9402b58bab4e
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Linked notes

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