3-(1-Pyrrolidinyl)-2-cyclopenten-1-one → HCID 22996624, compound

HRID 1167377Notes

Reaction equation

HRID 1167377 reaction equation
[N:1]1([C:6]2[CH2:10][CH2:9][C:8](=O)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1.N1([Ti](N2CCCC2)(N2CCCC2)N2CCCC2)CCCC1>[N:1]1([C:6]2[CH2:10][CH:9]=[C:8]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 2734983-(1-Pyrrolidinyl)-2-cyclopenten-1-one

Product 1

HCID 22996624HCID 22996624, compoundYield 181.3%

Reagents, catalysts & solvents 2

HCID 178420624HCID 178420624, compoundCatalystHCID 1140TolueneSolvent

Procedure

To 2.245 g (14.85 mmol) of 3-(pyrrolidino)-2-cyclopenten-1-one dissolved in 50 mL of toluene was added 2.5 g (7.61 mmol) of the tetrapyrrolidino titanium. The reaction mixture became red with concomitant appearance of precipitate. The reaction mixture was stirred overnight and then filtered giving a dark red solution. Toluene was removed under reduced pressure to give 2.75 g of red crystalline solid. Yield was 90.6 percent. This product was then recrystallized from 60 mL of hexane to give 1.56 g of the desired product as large red-orange crystals.

Workup

  1. filtrationfiltered
  2. customgiving a dark red solution
  3. customToluene was removed under reduced pressure

Sources & evidence

ORD record
ord-6b0b39bea0084d37991724765d64ef51
Source dataset
uspto-grants-2003_09
Patent number
US06617407B1

Reaction notes

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