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(3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione → (1RS,3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrile

HRID 2293301
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2293301
[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]2[CH:10]([C:11]([CH3:27])([CH3:26])[N:12]([CH3:25])[CH:13]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cu][C:30]#[N:31]>CN(C=O)C>[CH2:1]([N:8]1[C:9](=[O:28])[CH:10]2[C:11]([CH3:27])([CH3:26])[N:12]([CH3:25])[CH:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:30]#[N:31])=[CH:20][CH:19]=3)[CH:14]2[C:15]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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Komponenten

4

Edukt 2

HCID 69953772(3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dioneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 69954349(1RS,3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrileAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3.45 g (7.82 mmol) of (3aRS,4RS,6aSR)-2-benzyl-4-(4-bromobenzyl)-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione and 3.52 g (39.1 mmol) of copper(I) cyanide were suspended in 150 ml of DMF under argon and heated under reflux for 56 hours. After cooling about 100 ml of DMF were removed, then 150 ml of dichloromethane and 60 ml of concentrated aqueous ammonia solution were added. The mixture was stirred vigorously for a few hours. The blue aqueous phase was separated and the organic phase was washed twice with ammonia solution and once with water. The solvent was removed and the residue was purified chromatographically (hexane/ethyl acetate 1:1+1% triethylamine). 1.91 g of (1RS,3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrile were isolated as a yellowish oil. FAB-MS: 775 ([2M+H]+, 1); 663 (2); 388 ([M+H]+, 58); 271 (100); 91 (42).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 56 hours
  3. customwere removed
  4. addition150 ml of dichloromethane and 60 ml of concentrated aqueous ammonia solution were added
  5. customThe blue aqueous phase was separated
  6. washthe organic phase was washed twice with ammonia solution and once with water
  7. customThe solvent was removed
  8. customthe residue was purified chromatographically (hexane/ethyl acetate 1:1+1% triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-af072824ef7446f68c4e4d1ab6f81f13
Quelldatensatz
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05686459

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