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

HRID 2115292Notes

Reaction equation

HRID 2115292 reaction equation
[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]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 4171147tert-Butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cc3d58b5de02434fad6cc75ce0cde871
Source dataset
uspto-grants-2008_10
Patent number
US07435831B2

Reaction notes

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