Sodium Cyanide → HCID 178454087, Verbindung

HRID 628356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628356
CS(O[C@H:6]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[C-:18]#[N:19].[Na+]>CN(C=O)C>[C:18]([C@H:6]1[CH2:9][C@H:8]([NH:10][C:11](=[O:12])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1)#[N:19]

Komponenten

4

Edukt 2

HCID 8929Sodium Cyanide2×HCID 178454135HCID 178454135, Verbindung

Produkt 1

HCID 178454087HCID 178454087, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

cis-3-[(tert-Butoxycarbonyl)amino]cyclobutyl methanesulfonate (0.200 g, 0.754 mmol) in DMF (3 mL) was treated with NaCN (55 mg, 1.13 mmol, Aldrich) and the reaction was heated in the microwave to 140° C. for 10 minutes, followed by stirring overnight at 125° C. with an additional 55 mg (1.13 mmol) of NaCN having been added. The reaction mixture was partitioned between saturated NaHCO3 solution and EtOAc. The aqueous layer was extracted three additional times with EtOAc. The combined extracts were dried over sodium sulfate, decanted, and the solvent was removed in vacuo. Flash chromatography, eluting with a gradient from 0-50% EtOAc in hexanes, afforded tert-butyl (trans-3-cyanocyclobutyl)carbamate. Yield: (61 mg, 41%).

Aufarbeitung

  1. additionbeen added
  2. customThe reaction mixture was partitioned between saturated NaHCO3 solution and EtOAc
  3. extractionThe aqueous layer was extracted three additional times with EtOAc
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. customthe solvent was removed in vacuo
  7. washFlash chromatography, eluting with a gradient from 0-50% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d6736b86da054e7bb6cf4d5812f37937
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309246B2

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