HCID 18447315, compound → HCID 22934086, compound

HRID 1269904Notes

Reaction equation

HRID 1269904 reaction equation
[O-]CC.[Na+].C(O)C.[CH2:8]([N:15]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:8]([N:15]1[CH2:16][CH2:17][CH2:18][CH:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:26](=[O:28])[CH2:25]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:8]([N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[CH:25]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 18447315HCID 18447315, compoundHCID 23706232Ethanol sodium ethoxide2×

Product 2

HCID 22933378HCID 22933378, compoundYield 19%HCID 22934086HCID 22934086, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under a nitrogen atmosphere, a 21% wt. sodium ethoxide-ethanol solution (1.23 ml, 3.31 mmol) was added to toluene (100 ml) at room temperature, and the resulting mixture was refluxed by the use of a Dean-Stark trap. A solution of ethyl 5-[benzyl(2-ethoxy-2-oxoethyl)amino]pentanoate (965.9 mg, 3.01 mmol) in toluene (50 ml) was added dropwise thereto over a period of 1.5 hours. After 3 hours, a 21% wt. sodium ethoxide-ethanol solution (1.23 ml, 3.31 mmol) was further added thereto. After another 1 hour, the toluene (30 ml) was distilled off with heating. After 5 hours, the reaction solution was poured into water (200 ml) and extracted with ethyl acetate (100 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain ethyl 1-benzyl-3-oxoazepane-4-carboxylate (158.5 mg, 19%) and ethyl 1-benzyl-3-oxoazepane-2-carboxylate (213.8 mg, content=about 75%).

Workup

  1. temperaturethe resulting mixture was refluxed by the use of a Dean-Stark trap
  2. waitAfter 3 hours
  3. waitAfter another 1 hour
  4. distillationthe toluene (30 ml) was distilled off
  5. temperaturewith heating
  6. waitAfter 5 hours
  7. additionthe reaction solution was poured into water (200 ml)
  8. extractionextracted with ethyl acetate (100 ml×2)
  9. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  10. customThe organic layer dried
  11. concentrationwas concentrated under reduced pressure
  12. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3473f74d0d4c4ec9a83a97dda7f226e1
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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