Aluminium lithium hydride → 2-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridine

HRID 712467Notes

Reaction equation

HRID 712467 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:22](=O)[CH:21]2[CH:16]([CH2:17][NH:18][CH2:19][CH2:20]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:22][CH:21]2[CH:16]([CH2:17][NH:18][CH2:19][CH2:20]2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22646963Hexahydro-2-(phenylmethyl)-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione

Product 1

HCID 219789862-Benzyloctahydro-1H-pyrrolo[3,4-c]pyridineYield 25.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiAlH4 (1.00 g) in THF was added slowly 2-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-dione (2.00 g) at 0° C. The reaction mixture was refluxed for 6 h under N2, and cooled to rt, quenched with ice-water and filtered. The filtrate was concentrated in vacuo to give the title compound as yellow oil (0.45 g, 25%). The crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.2 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h under N2
  2. customquenched with ice-water
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ec5cc4237a224950ac30ec8d30f9a10c
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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