2-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione → rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

HRID 1872025ノート

反応式

HRID 1872025 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:21](=O)[CH:20]2[CH:16]([CH2:17][NH:18][CH2:19]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:15][C@@H:16]2[C@@H:20]([CH2:19][NH:18][CH2:17]2)[CH2:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 129585072-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 1514450rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Lithium aluminium hydride (1M in THF, 85 ml, 85 mmol) was added slowly to a stirred solution of 2-benzyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione (6.4 g, 27.8 mmol) in dry tetrahydrofuran (60 ml) at room temperature under nitrogen. Upon complete addition, the mixture was stirred and heated at 70° C. for 16 h. The mixture was then cooled to 0° C. and carefully quenched with water (3.2 ml), followed by 4N sodium hydroxide (3.2 ml) and water (4.5 ml). The mixture was filtered, washing with ethyl acetate. The filtrate was evaporated and the residue was purified by chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1) to give the title amine (4.5 g, 80%) as a clear oil. 1H NMR δ (360 MHz, CDCl3) 2.24-2.28 (2H, m), 2.42 (1H, s), 2.56-2.64 (4H, m), 2.68 (1H, dd, J=11.5. 2.4 Hz), 2.77-2.83 (2H, m), 3.44 (2H, s, CH2Ph), 7.13-7.30 (5H, m, Ar--H). 13C NMR δ (90.5 MHz, CDCl3) 43.6 (CH), 54.4 (CH2), 59.9 (CH2), 60.8 (CH2), 126.8 (CH), 128.2 (CH), 128.8 (CH), 139.3 (C).

後処理

  1. additionUpon complete addition
  2. temperatureThe mixture was then cooled to 0° C.
  3. customcarefully quenched with water (3.2 ml)
  4. filtrationThe mixture was filtered
  5. washwashing with ethyl acetate
  6. customThe filtrate was evaporated
  7. customthe residue was purified by chromatography on silica gel
  8. washeluting with CH2Cl2 /MeOH/NH3 (40:8:1→30:8:1)

出典と根拠

ORDレコード
ord-9ec458e8e8b546989ceaf09f80a0e423
出典データセット
uspto-grants-2000_08
特許番号
US06107321

反応ノート

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