Sodium Methoxide → methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

HRID 1358095Notes

Reaction equation

HRID 1358095 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([N:11]1[C:16](=[O:17])[CH:15]2[CH2:18][CH:12]1[CH:13]=[CH:14]2)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>CO>[CH3:1][O:2][C:16]([C:15]1[CH2:18][C@@H:12]([NH:11][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:13][CH:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15319948Tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Product 1

HCID 10490292methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide (8.23 ml of a 25% wt solution in methanol, 0.05 mol eq) was added dropwise to a stirred solution of (−)-N-Boc 2-azabicyclo[2.2.1]hept-5-en-3-one (150 g, 0.72 mol) in methanol (750 ml) at 0° C. After 30 minutes, the reaction was warmed to room temperature. After 60 h, the reaction was quenched with acetic acid and concentrated to dryness. The residue was redissolved in dichloromethane (700 ml) and washed with water (300 ml), saturated sodium hydrogen carbonate (300 ml) and brine (300 ml). The combined aqueous washings were then back extracted with dichloromethane (300 ml), the organic extracts combined and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave a white solid which was recrystallized from ethyl acetate/heptane to give the title compound as white crystals (130 g, 75%)

Workup

  1. waitAfter 60 h
  2. customthe reaction was quenched with acetic acid
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was redissolved in dichloromethane (700 ml)
  5. washwashed with water (300 ml), saturated sodium hydrogen carbonate (300 ml) and brine (300 ml)
  6. extractionThe combined aqueous washings were then back extracted with dichloromethane (300 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and concentration under reduced pressure
  9. customgave a white solid which
  10. customwas recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-f9a9c7240caf4b609b9771c3fb500b37
Source dataset
uspto-grants-2003_07
Patent number
US06593489B1

Reaction notes

Loading…