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1,4-Dibromobenzene → tert-Butyl(3aR,6aR)-1-(4-bromophenyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

HRID 12969
ノート
印刷プレビュー

反応式

HRID 12969 の反応式
[NH:1]1[CH2:5][CH2:4][C@@H:3]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@H:2]12.[Br:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:1]2[CH2:5][CH2:4][C@@H:3]3[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@H:2]23)=[CH:19][CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 78041,4-DibromobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 37818785tert-butyl (3aR,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[2,3-c]pyrrole-5-carboxylate

生成物 1

HCID 59339923tert-Butyl(3aR,6aR)-1-(4-bromophenyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

試薬・触媒・溶媒 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒

反応条件

温度
140 °C

実験手順

tert-Butyl(3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (1, 1.5 g, 7.0 mmol), 1.4-dibromobenzene (2.8 g, 20.4 mmol), Pd2(dba)3 (275 mg, 0.3 mmol), BINAP (375 mg, 0.6 mmol) and sodium tert-butoxide (1.93 g, 20.0 mmol) were placed in glass microwave tubes and then purged three times with N2 gas, followed by the addition of toluene (45 mL). The mixture was heated to 140° C. for 15 minutes in a microwave reactor. The mixture was then cooled to room temperature, was filtered, and the crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ=7.30 ppm (m, 2H), 7.39 (m, 2H), 4.11 (m, 1H), 3.57 (m, 3H), 3.31 (m, 3H), 2.99 (m, 1H), 2.15 (m, 1H), 1.92 (m, 1H), 1.43 (s, 9H). MS (ESI, M+1): 310.9.

後処理

  1. custompurged three times with N2 gas
  2. additionfollowed by the addition of toluene (45 mL)
  3. temperatureThe mixture was then cooled to room temperature
  4. filtrationwas filtered
  5. customthe crude mixture was purified via chromatography (SiO2, 0-25% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-922d3082846945a38837d1de7079dd7e
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07728031B2

反応ノート

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