Water → HCID 21084207, compound

HRID 347812Notes

Reaction equation

HRID 347812 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[NH:2]2.C(N(CC)CC)C.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.O>C(Cl)(Cl)Cl>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:2]2[CH:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]3[CH2:7][CH:1]2[CH2:6][CH2:5]3)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 13258847Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate

Product 1

HCID 21084207HCID 21084207, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate (231 mg, 1.37 mmol) in chloroform (5 ml) were added triethylamine (0.20 ml, 1.43 mmol) and 4-methoxybenzyl chloride (0.19 ml, 1.43 mmol) while being cooled with ice. After a reaction at 60° C. for 20 hours, the reaction mixture, with water added thereto, was extracted with chloroform. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (1% methanol/chloroform), to give ethyl 2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (340 mg, 86%).

Workup

  1. temperaturewhile being cooled with ice
  2. customAfter a reaction at 60° C. for 20 hours
  3. extractionwas extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-056699029390416ba63af9995e511993
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

Loading…