HCID 178454124, Verbindung → HCID 178454110, Verbindung

HRID 707264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707264
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:11][C@@H:10]([N:12]=[N+]=[N-])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 1

HCID 178454124HCID 178454124, Verbindung

Produkt 1

HCID 178454110HCID 178454110, VerbindungAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A mixture of tert-butyl(cis-3-azidocyclobutyl)carbamate (7.0 g, 33.0 mmol) and palladium 10% on activated carbon (3.51 ml, 33.0 mmol) in a three necked 1000 mL flask was flushed with nitrogen and 2M ammonia in methanol solution (200 mL) was added. The flask was evacuated and a balloon filled with hydrogen was introduced. The mixture was stirred at room temperature for 18 h, filtered, and the filtrate was evaporated under reduced pressure to give the desired product tert-butyl(cis-3-aminocyclobutyl)carbamate (6.1 g, 99% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.64 (br. s., 1 H), 3.72 (d, J=6.85 Hz, 1 H), 3.12 (t, J=7.73 Hz, 1 H), 2.71 (d, J=7.24 Hz, 2 H), 1.51 (q, J=9.85 Hz, 2 H), 1.43 (br. s., 11 H).

Aufarbeitung

  1. customwas flushed with nitrogen and 2M ammonia in methanol solution (200 mL)
  2. additionwas added
  3. customThe flask was evacuated
  4. additiona balloon filled with hydrogen
  5. additionwas introduced
  6. filtrationfiltered
  7. customthe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-adeca629a6e6467e85bb920ba0798b5e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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