Sodium Carbonate → Methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate

HRID 1515349Notes

Reaction equation

HRID 1515349 reaction equation
[NH2:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[C:27](=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O>[CH2:20]([O:19][C:17](=[O:18])[CH2:27][NH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate2×HCID 57425932Methyl 4-aminoadamantane-1-carboxylate

Product 1

HCID 68520083Methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-aminoadamantane-1-carboxylate obtained in Reference Example 11 (1.87 g) in tetrahydrofuran (20 ml), water (10 ml), benzyl chloroformate (1.53 g) and sodium carbonate (1.13 g) were added and stirred at room temperature for 5 hours. Benzyl chloroformate (0.76 g) was further added and stirred at room temperature for 2 hours. After insoluble materials were filtered off, the solvent was concentrated and the residue was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1) to give methyl 4-{[2-(benzyloxy)-2-oxoethyl]amino}-adamantane-1-carboxylate (3.30 g) as a colorless powder.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for 2 hours
  3. filtrationAfter insoluble materials were filtered off
  4. concentrationthe solvent was concentrated
  5. extractionthe residue was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customto remove the desiccant
  9. distillationby distilling off the solvent under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=200:1 to 100:1)

Sources & evidence

ORD record
ord-8912306657ff4f32a49c1ff8bdc8eddc
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

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