Trimethylsilyl iodide → 2-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione

HRID 56408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56408
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@H:12]1[C@@H:17]([NH:18]C(=O)OCC2C=CC=CC=2)[CH2:16][C@H:15]2[C@@H:13]1[CH2:14]2.C[Si](I)(C)C>C(Cl)(Cl)Cl>[NH2:18][C@H:17]1[CH2:16][C@H:15]2[C@H:13]([CH2:14]2)[C@H:12]1[N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 118048962benzyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate

Produkt 1

HCID 1180362842-((1S,2R,3S,5S)-3-aminobicyclo[3.1.0]hexan-2-yl)isoindoline-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of benzyl (1S,2R,3S,5S)-2-(1,3-dioxoisoindolin-2-yl)bicyclo[3.1.0]hexan-3-ylcarbamate (4.0 g, 10.638 mmol) in chloroform (30 mL) at room temperature was added trimethylsilyl iodide (14.6 mL, 106.380 mmol) dropwise, and the resulting mixture was stirred at room temperature for 1 hour. The reaction was quenched with methanol (5 mL), diluted with ethyl acetate (150 mL), and washed with water (3×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford a crude compound, which was directly used in the next reaction without further purification. MS (ES+) C14H14N2O2 requires: 242, found: 243 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with methanol (5 mL)
  2. additiondiluted with ethyl acetate (150 mL)
  3. washwashed with water (3×50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b6b9d5443544f8d86e6865dc3d72cb1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434700B2

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