N-benzyl-3-chloro-N-(2-methylallyl)-1,2-dihydrocyclobutabenzene-1-carboxamide → trans-2-benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one

HRID 1026627ノート

反応式

HRID 1026627 の反応式
[CH2:1]([N:8]([CH2:20][C:21]([CH3:23])=[CH2:22])[C:9]([CH:11]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>BrC1C=CC=CC=1>[CH2:1]([N:8]1[C:9](=[O:10])[C@@H:11]2[C@:21]([CH3:22])([CH2:23][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=32)[CH2:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 70664766N-benzyl-3-chloro-N-(2-methylallyl)-1,2-dihydrocyclobutabenzene-1-carboxamide

生成物 1

HCID 70665184trans-2-benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one収率 12.3%

試薬・触媒・溶媒 1

HCID 7961Bromobenzene溶媒

実験手順

A solution of N-benzyl-3-chloro-N-(2-methylallyl)-1,2-dihydrocyclobutabenzene-1-carboxamide (5.52 mmol, 1.8 g) in bromobenzene (21 ml) was irradiated in a microwave for 30 min at 210 degrees. The bromobenzene was removed under reduced pressure and then purified by flash chromatographed using ethyl acetate in heptane (10 to 20%) to afford trans-2-benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (221 mg, 12% yield), followed by cis-2-benzyl-6-chloro-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-1-one (649 mg, 36% yield).

後処理

  1. customThe bromobenzene was removed under reduced pressure
  2. custompurified by flash
  3. customchromatographed

出典と根拠

ORDレコード
ord-45f78ba227804ec7bf177ba8d35e2084
出典データセット
uspto-grants-2014_05
特許番号
US08729274B2

反応ノート

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