HCID 13288028, compound → HCID 12804791, compound

HRID 1106056Notes

Reaction equation

HRID 1106056 reaction equation
[CH:1]([N:3]1[CH2:7][CH2:6][C:5]([OH:21])([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>C1COCC1>[OH:21][C:5]1([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)[CH2:6][CH2:7][N:3]([CH3:1])[CH2:4]1

Participants

3

Reactant 1

HCID 13288028HCID 13288028, compound

Product 1

HCID 12804791HCID 12804791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.90 g of 1-formyl-3-hydroxy-3-(α-phenyl-2-tolyl)pyrrolidine in 60 ml of dry THF is added dropwise to a suspension of 3 g of LiAlH in 30 ml of dry THF and the mixture is refluxed for 4 hours. After cooling the mixture is separated and the residue extracted with ether. The combined organic solution is dried (Na2SO4) and concentrated to an oil. This oil is dissolved in 100 ml of hexane and after cooling 16 hours the product is isolated by filtration to provide 3-hydroxy-1-methyl-3-(α-phenyl-2-tolyl)pyrrolidine, mp 108°-109° C. Dilution of the mother liquor with 50 ml of hexane gives a second crop of 3-hydroxy-1-methyl-3-(α-phenyl-2-tolyl)pyrrolidine, mp 107°-108° C.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling the mixture
  3. customis separated
  4. extractionthe residue extracted with ether
  5. dry with materialThe combined organic solution is dried (Na2SO4)
  6. concentrationconcentrated to an oil
  7. dissolutionThis oil is dissolved in 100 ml of hexane
  8. temperatureafter cooling 16 hours the product
  9. customis isolated by filtration

Sources & evidence

ORD record
ord-c116cf1047164410a79aa713dd5f41fc
Source dataset
uspto-grants-1982_01
Patent number
US04311703

Reaction notes

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