HCID 91290871, compound → HCID 18630842, compound

HRID 1060186Notes

Reaction equation

HRID 1060186 reaction equation
C(O[C:4](=[O:28])[CH2:5][N:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15]C(OCC)=O)[CH:10]=[CH:11][CH:12]=1)C.O(C)[Na]>>[C:22]1([CH2:21][N:6]2[CH:7]([CH2:12][C:11]3[CH:10]=[CH:9][CH:13]=[CH:14][CH:15]=3)[CH2:8][C:4](=[O:28])[CH2:5]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 91290871HCID 91290871, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 18630842HCID 18630842, compoundYield 14.7%

Conditions

Temperature
80 °C

Procedure

Intermediate 21 (0.2 mol) was heated to 80° C. under N2 flow. NaOCH3 (44 g) was added. The mixture was stirred at 80° C. for 30 minutes. The solvent was evaporated and water (170 ml) and HCl (6N, 60 ml) were added. The mixture was stirred and refluxed for 1 hour, then cooled, alkalized with NaOH and extracted with CH2Cl2. The organic layer was separated, washed with water and a saturated NaCl solution, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3CN 100/0 to 96/4). The pure fractions were collected and the solvent was evaporated, yielding 7.8 g of (±)-1,5-bis(phenylmethyl)-3-pyrrolidinone (intermediate 22).

Workup

  1. customThe solvent was evaporated
  2. additionwater (170 ml) and HCl (6N, 60 ml) were added
  3. stirringThe mixture was stirred
  4. temperaturerefluxed for 1 hour
  5. temperaturecooled
  6. extractionextracted with CH2Cl2
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materiala saturated NaCl solution, dried
  10. filtrationfiltered
  11. customthe solvent was evaporated
  12. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3CN 100/0 to 96/4)
  13. customThe pure fractions were collected
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f3f1eeed10ac495393e2b7373046d23a
Source dataset
uspto-grants-2003_02
Patent number
US06521621B1

Reaction notes

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