Ethanol → HCID 68593715, compound

HRID 383922Notes

Reaction equation

HRID 383922 reaction equation
Cl.[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[C:12]([OH:14])=[O:13])[CH2:3]1)[CH2:9]2.S(=O)(=O)(O)O.[CH3:20][CH2:21]O>>[N:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[C:12]([O:14][CH2:20][CH3:21])=[O:13])[CH2:3]1)[CH2:9]2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 68592832HCID 68592832, compound

Product 1

HCID 68593715HCID 68593715, compound

Procedure

To a solution of 1-azatricyclo[3.3.1.13,7]decane-4-carboxylic acid hydrochloride in EtOH was added concentrated sulfuric acid, followed by heating under reflux for 18 hours. The reaction liquid was concentrated under reduced pressure and then diluted with EtOAc. The EtOAc layer was washed with an aqueous NaHCO3 solution and brine in this order, dried over MgSO4, and then concentrated under reduced pressure to obtain a yellow oily substance. This was purified by silica gel column chromatography (CHCl3:MeOH) to obtain ethyl 1-azatricyclo[3.3.1.13,7]decane-4-carboxylate as a yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. additiondiluted with EtOAc
  6. washThe EtOAc layer was washed with an aqueous NaHCO3 solution and brine in this order
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a yellow oily substance
  10. customThis was purified by silica gel column chromatography (CHCl3:MeOH)

Sources & evidence

ORD record
ord-1a2b38b7893a4801ba20856e0bada30c
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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