Triethylamine → HCID 57058580, compound

HRID 846615Notes

Reaction equation

HRID 846615 reaction equation
Br[CH:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]([C:31]1[CH:32]=[C:33]([C:42]2[N:43]=[C:44]([CH:47]=O)[S:45][CH:46]=2)[CH:34]=[C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])[C:36]=1[OH:37])([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>C(OC(=O)C)(=O)C>[C:27]([C:31]1[CH:32]=[C:33]([C:42]2[N:43]=[C:44]([CH:47]=[C:2]3[CH2:6][CH2:5][NH:4][C:3]3=[O:7])[S:45][CH:46]=2)[CH:34]=[C:35]([C:38]([CH3:39])([CH3:40])[CH3:41])[C:36]=1[OH:37])([CH3:28])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 101034713-Bromopyrrolidin-2-oneHCID 19883549HCID 19883549, compound

Product 1

HCID 57058580HCID 57058580, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

16.0 g (91 mmol) of 3-bromopyrrolidin-2-one were heated to boiling in 30 ml of acetic anhydride for 1 hour. After evaporating the reaction mixture t dryness under reduced pressure, the residue was dissolved in 50 ml of tetrahydrofuran and, after adding 26.2 g (0.1 mol) of triphenylphosphine, heated under reflux for 5 hours. It was then concentrated again, the residue was dissolved in 300 ml of ethanol and 24.7 g (78 mmol) of the aldehyde from Example 2 b1) and 27 ml (0.36 mol) of triethylamine were added. After heating the mixture at 70° C. for 2 hours, the yellow precipitate was filtered off and washed with ethanol. The crystal magma is dissolved in about 2 1 of chloroform, the solution is washed several times with saturated sodium chloride solution and dried over Na2SO4, and the chloroform phase is concentrated to a third. Yellow crystals deposit on allowing to stand for a relatively long time.

Workup

  1. customAfter evaporating the reaction mixture t dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml of tetrahydrofuran
  3. temperatureheated
  4. temperatureunder reflux for 5 hours
  5. concentrationIt was then concentrated again
  6. dissolutionthe residue was dissolved in 300 ml of ethanol
  7. filtrationthe yellow precipitate was filtered off
  8. washwashed with ethanol
  9. dissolutionThe crystal magma is dissolved in about 2 1 of chloroform
  10. washthe solution is washed several times with saturated sodium chloride solution
  11. dry with materialdried over Na2SO4
  12. concentrationthe chloroform phase is concentrated to a third

Sources & evidence

ORD record
ord-55a7682b6c96497a96dc101d6178bd4f
Source dataset
uspto-grants-1992_08
Patent number
US05137897

Reaction notes

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