Ammonium formate → Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

HRID 2115292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2115292
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][N:12](CC3C=CC=CC=3)[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:14]([CH2:13][NH:12][CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 4171147Tert-butyl 5-benzyl-octahydropyrrolo[3,4-c]pyrrole-2-carboxylate

Produkt 1

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of compound 4 (130 mg), Pd/C (100 mg, 10%) and ammonium formate (160 mg) in ethanol (10 mL) was heated to reflux for 2 hours and then allowed to cool to room temperature. The solid was filtered off and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC to provide title compound 5 as a pale yellow oil (76 mg, 84%). LCMS: Rf: 0.371 min, M+H+: 213.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cc3d58b5de02434fad6cc75ce0cde871
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435831B2

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