HCID 91290871, compound → HCID 18630842, compound

HRID 1530921Notes

Reaction equation

HRID 1530921 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 and 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 and 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. extractionNaOH and extracted 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 and 96/4)
  13. customThe pure fractions were collected
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9985283a40b64a14bd7a3beaff26c304
Source dataset
uspto-grants-2001_03
Patent number
US06197772B1

Reaction notes

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