Dabco → HCID 19767594, compound

HRID 1590585Notes

Reaction equation

HRID 1590585 reaction equation
N12CCN(CC1)CC2.[CH2:9]([N:11]([CH2:28]C)[C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:21]2[CH2:25][CH:24]([OH:26])[CH2:23][C:22]2=[O:27])(=[O:20])=[O:19])=[CH:14][CH:13]=1)C.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][N:11]([CH3:9])[C:12]1[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:25][CH:24]([O:26][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][C:22]2=[O:27])(=[O:19])=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 9237Dabco2×HCID 62493Pivaloyl chloride2×HCID 19767579HCID 19767579, compound

Product 1

HCID 19767594HCID 19767594, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.41 g of 1,4-diazabicyclo [2.2.2]octane (DABCO) is added at 3° C. to a solution of 1 g of [1-(4-diethylamino-benzenesulphonyl)-4-hydroxy-pyrrolidin-2-one] in 20 cm3 of methylene chloride, and then 0.43 g of pivaloyl chloride in solution in 3 cm3 of methylene chloride is added slowly, and the whole mixture is left at ambient temperature for 16 hours. Another equivalent of pivaloyl chloride and DABCO is added, the mixture is left at ambient temperature for 4 hours, brought to dryness, the residue is taken up in ethyl acetate, washed with water (at a pH of about 6), followed by filtering and bringing to dryness under reduced pressure, and the residue is chromatographed on silica (eluant: ethyl acetate - hexane 4-1). 0.6 g of expected crude product and 0.3 g of product containing a double bond in position 3,4 of the pyrrolidinone are obtained. The crude product is added to a previous preparation in order to obtain, after recrystallization from an ethyl acetate - hexane mixture (3-50), 0.86 g of the desired product. M.p.=117-118° C.

Workup

  1. waitthe mixture is left at ambient temperature for 4 hours
  2. washwashed with water (at a pH of about 6),
  3. filtrationby filtering
  4. customthe residue is chromatographed on silica (eluant: ethyl acetate - hexane 4-1)
  5. addition0.6 g of expected crude product and 0.3 g of product containing a double bond in position 3,4 of the pyrrolidinone
  6. customare obtained
  7. customto obtain
  8. customafter recrystallization from an ethyl acetate - hexane mixture (3-50), 0.86 g of the desired product

Sources & evidence

ORD record
ord-cce0848c162a49fabf05a3e0ecc3f64e
Source dataset
uspto-grants-1993_04
Patent number
US05204341

Reaction notes

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