5-Benzyl-4,6-dioxooctahydropyrrolo[3.4-c]pyridine → 5-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridine

HRID 1893Notes

Reaction equation

HRID 1893 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:19](=O)[CH2:18][CH:17]2[CH2:21][NH:22][CH2:23][CH:16]2[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC.C(Cl)Cl>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]2[CH2:21][NH:22][CH2:23][CH:16]2[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 196913995-Benzyl-4,6-dioxooctahydropyrrolo[3.4-c]pyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 225622165-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridineYield 81.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

A suspension of 266 mg of LAH in 10 mL of ether was stirred at 10° C. under N2. To this suspension was added 540 mg of the compound from step 457d dissolved in 10 mL of methylene chloride. The mixture was stirred under N2 for 1.5 hours. The reaction was quenched by the sequential dropwise addition of 0.3 mL water, 0.3 mL of 15% NaOH and 0.6 mL of water, then the mixture was stirred for 1 hour and filtered. The filtrate was dried and concentrated to give 389 mg of the title compound.

Workup

  1. stirringThe mixture was stirred under N2 for 1.5 hours
  2. customThe reaction was quenched by the sequential dropwise addition of 0.3 mL water, 0.3 mL of 15% NaOH and 0.6 mL of water
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationfiltered
  5. customThe filtrate was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-88b5cc36e3014d199d30d93dc27d1375
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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