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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
ノート
印刷プレビュー

反応式

HRID 2293301 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-af072824ef7446f68c4e4d1ab6f81f13
出典データセット
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05686459

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート