4-Cyanobenzaldehyde → HCID 69955377, compound

HRID 2293307Notes

Reaction equation

HRID 2293307 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1C(O)=O.[C:9]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[N:10].[CH2:19]([N:26]1[C:30](=[O:31])[CH:29]=[CH:28][C:27]1=[O:32])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:26]1[C:30](=[O:31])[CH:29]2[CH:15]([C:14]3[CH:17]=[CH:18][C:11]([C:9]#[N:10])=[CH:12][CH:13]=3)[N:1]3[CH:2]([CH:28]2[C:27]1=[O:32])[CH2:6][CH2:7][CH2:8]3)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 74204BenzylmaleimideHCID 145742L-Proline

Product 1

HCID 69955377HCID 69955377, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4.B)f) A mixture of L-proline (20 mmol), 4-cyano-benzaldehyde (20 mmol) and N-benzylmaleimide (20 mmol) in DMF (20 ml) was heated to 80° C. for 5 hours. The solvent was removed in a high vacuum and the residue was separated chromatographically over silica gel (eluent hexane:ethyl acetate=1:1+1% triethylamine). (3aRS,4SR,8aRS,8bSR)-4-(2-Benzyl-1,3-dioxo-decahydro-pyrrolo[3,4-a]pyrrolizin-4-yl)-benzonitrile was isolated in 32% yield as colourless crystals. M.p.: 191°-193° C. (methanol). EI-MS: 371 ([M]+, 7); 184 (100); 156 (11); 91 (12)

Workup

  1. customThe solvent was removed in a high vacuum
  2. customthe residue was separated chromatographically over silica gel (eluent hexane:ethyl acetate=1:1+1% triethylamine)

Sources & evidence

ORD record
ord-e2eb71e764c24d1eb576e237ad3b891c
Source dataset
uspto-grants-1997_11
Patent number
US05686459

Reaction notes

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