2-Azabicyclo(2.2.1)hept-5-en-3-one → HCID 10910778, compound

HRID 1241353Notes

Reaction equation

HRID 1241353 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.[C:9](=O)([O:15]C(C)(C)C)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]>O1CCCC1.CN(C)C1C=CN=CC=1>[O:8]=[C:3]1[C@@H:4]2[CH2:7][C@@H:1]([CH:6]=[CH:5]2)[N:2]1[C:9]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:15]

Participants

5

Reactant 2

HCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-oneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 10910778HCID 10910778, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one (Chiroscience, Cambridge, England; 54.565 g, 0.500 mole) was dissolved in dry tetrahydrofuran (350 ml). Di-tert-butyl carbonate (Aldrich, 114.87 g, 0.510 mole as 97%) and 4-dimethylaminopyridine (Aldrich, 600 mg) were added to the stirred mixture. The resulting solution was stirred at ambient temperature for 2 hours. Solvent was evaporated under reduced pressure and the residual orange solid was crystallized from toluene-hexanes to give title compound as white crystals (95.72 g, 91%), m.p. 85–86° C.; 1H-NMR (CDCl3) δ 1.50 (s, 9H), 2.24 (app AB q, J=8.4 Hz, 2H), 3.39 (br s, 1H), 4.96 (m, 1H), 6.66 (m, 1H), 6.89 (m, 1H).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. customthe residual orange solid was crystallized from toluene-hexanes

Sources & evidence

ORD record
ord-968b80dfe26e48faac822c1c8fef5679
Source dataset
uspto-grants-2006_10
Patent number
US07115590B1

Reaction notes

Loading…