Cyclooctane-1,5-dione → HCID 18767736, compound

HRID 2105663Notes

Reaction equation

HRID 2105663 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10](CN3CCCC3)[CH:9]=[N:8][C:7]=2[N:6]([CH2:20][CH2:21][CH3:22])[C:5]1=[O:23])[CH2:2][CH3:3].[Li]CCCC.[C:29]1(=[O:38])[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH2:32][CH2:31][CH2:30]1>C1COCC1>[OH:37][C:33]12[O:38][C:29]([C:9]3[NH:10][C:11]4[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:23])[N:6]([CH2:20][CH2:21][CH3:22])[C:7]=4[N:8]=3)([CH2:36][CH2:35][CH2:34]1)[CH2:30][CH2:31][CH2:32]2

Participants

5

Reactant 3

HCID 281640Cyclooctane-1,5-dioneHCID 18767636HCID 18767636, compoundHCID 178418339Butyllithium

Product 1

HCID 18767736HCID 18767736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1,3-Dipropyl-7-pyrrolidin-1-ylmethyl-3,7-dihydro-purine-2,6-dione (638 mg) was taken in dry THF (10 ml) at −78° C. nBuLi (0.88 ml, 2.5M in hexane) was added slowly. The reaction mixture turned orange and stirred for 30 min at −78° C. Cyclooctane-1,5-dione (280 mg) was dissolved in 3 ml of dry THF, added to the reaction mixture. Stirred at −78° C. for 30 min, slowly warmed to rt and stirred overnight. The reaction mixture was quenched with sat NH4Cl and extracted with ethyl acetate (3×50 ml). Combined organic layer was washed with 1N HCl, water, and brine. Dried over anhydrous Na2SO4 and concentrated. The crude product was purified on silica column, eluted with ethyl acetate:hexane (1:1). Mass (ES+ 377)

Workup

  1. additionwas added slowly
  2. additionadded to the reaction mixture
  3. stirringStirred at −78° C. for 30 min
  4. temperatureslowly warmed to rt
  5. stirringstirred overnight
  6. customThe reaction mixture was quenched with sat NH4Cl
  7. extractionextracted with ethyl acetate (3×50 ml)
  8. washCombined organic layer was washed with 1N HCl, water, and brine
  9. dry with materialDried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. customThe crude product was purified on silica column
  12. washeluted with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-5050aec35e3f42da9547b47a0321164d
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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