Water → HCID 12804802, compound

HRID 1106061Notes

Reaction equation

HRID 1106061 reaction equation
[CH:1]([N:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4]1)=O.O>C1COCC1>[CH3:1][N:3]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 962WaterHCID 12804798HCID 12804798, compound

Product 1

HCID 12804802HCID 12804802, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.90 g of 1-formyl-3-(α-phenyl-2-tolyl)pyrrolidine of Example 59 in 40 ml of dry THF is added dropwise to a suspension of 2 g LiAlH in 20 ml of dry THF and the mixture is refluxed for 4 hours. After cooling and hydrolyzing with 20 ml of H2O the organic phase is separated and the residue is extracted with ether. The combined organic phase is washed with water, dried (Na2SO4), and concentrated to an oil. This oil is dissolved in 10 ml of acetone and made acidic with a slight excess of HCl/ether. After addition of 200 ml of ether the product is collected and recrystallized from acetone/ether (35/70 ml) to provide 1-methyl-3-(α-phenyl-2-tolyl)pyrrolidine, mp 149.5°-151° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. customis separated
  3. extractionthe residue is extracted with ether
  4. washThe combined organic phase is washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to an oil
  7. dissolutionThis oil is dissolved in 10 ml of acetone
  8. additionAfter addition of 200 ml of ether the product
  9. customis collected
  10. customrecrystallized from acetone/ether (35/70 ml)

Sources & evidence

ORD record
ord-3587d971fde4417dbf6a8543f2fdd322
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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