Triethylamine → HCID 57779824, compound

HRID 552908Notes

Reaction equation

HRID 552908 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:21][C:22]([O:24][CH:25]1[CH2:29][C:28](=[O:30])[N:27]([CH2:31][C:32]2[CH:33]=[N:34][C:35]([Cl:38])=[CH:36][CH:37]=2)[C:26]1=O)=[O:23].C(N(CC)CC)C>C(#N)C>[Cl:38][C:35]1[N:34]=[CH:33][C:32]([CH2:31][N:27]2[C:28](=[O:30])[CH2:29][CH:25]3[O:24][C:22](=[O:23])[CH:21]=[C:26]23)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86632444HCID 86632444, compound

Product 1

HCID 57779824HCID 57779824, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

569 mg (2.17) of triphenylphosphine are added to 712 mg (1.97 mmol) of 1-[(6-chloropyridin-3-yl)methyl]-2,5-dioxopyrrolidin-3-yl bromoacetate (XI-1) in 40 ml of acetonitrile, and the mixture is stirred at 50° C. for 3 hours. 0.29 ml (2.08 mmol) of triethylamine is added, and the mixture is stirred at 50° C. for about 16 hours. The entire reaction mixture is concentrated under reduced pressure and the residue that remains is then taken up in a little ethyl acetate, the insoluble solid is filtered off and the filtrate is purified by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate. This gives 305 mg (59% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-6,6a-dihydro-2H-furo[3,2-b]pyrrol-2,5(4H)-dione.

Workup

  1. stirringthe mixture is stirred at 50° C. for about 16 hours
  2. customThe entire reaction mixture
  3. concentrationis concentrated under reduced pressure
  4. filtrationthe insoluble solid is filtered off
  5. customthe filtrate is purified by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-2c1832075c334d868b35a9b45017434b
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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