Water → 2-Benzyloctahydropyrrolo[3,4-c]pyrrole

HRID 2115291Notes

Reaction equation

HRID 2115291 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C:21](=O)[CH:20]2[CH:16]([CH2:17][NH:18][CH2:19]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1.ClCCl>[CH2:7]([N:14]1[CH2:15][CH:16]2[CH:20]([CH2:19][NH:18][CH2:17]2)[CH2:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 129585072-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 44543872-Benzyloctahydropyrrolo[3,4-c]pyrroleYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminum hydride (15.0 mL, 1.0 M solution in ether) was added dropwise to a solution of compound 2 (1.15 g) in THF (50 mL) and dichloromethane (40 mL) at 0° C. The reaction mixture was stirred an additional 1.5 hour at 0° C. and water (0.5 mL) was added followed by the addition of aqueous NaOH solution (0.5 mL, 20%) and then water (1.5 mL). The resulting solids was filtered off and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to provide the title compound 3 as a pale yellow oil (0.93 g, 92%). LCMS: Rf: 0.368 min, M+H+: 203.

Workup

  1. filtrationThe resulting solids was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e2844a1075424d979efa9753d739e7ee
Source dataset
uspto-grants-2008_10
Patent number
US07435831B2

Reaction notes

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