HCID 178418361, compound → Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dione

HRID 36670

Reaction equation

HRID 36670 reaction equation
[CH2:1]([N:8]=[C:9]([C:11]1[C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=[CH:13][N:12]=1)[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>COCCO.[Ru]>[CH2:1]([N:8]1[C:17](=[O:19])[CH:16]2[CH:11]([NH:12][CH2:13][CH2:14][CH2:15]2)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178524453HCID 178524453, compound

Product 1

HCID 9899604Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dioneYield 90.1%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

47.6 g (0.2 mol) of pyridine-2,3-dicarboxylic acid N-benzylimide (British Patent 1,086,637; Chem. Abstr. 68, 95695w) are hydrogenated in 400 ml of glycol monomethyl ether over 15 g of ruthenium-on-active charcoal (5% strength) at 90° C. under 100 bar until the calculated amount of hydrogen has been taken up. The catalyst is then filtered off and the filtrate is concentrated on a rotary evaporator. 44 g of an oily crude product are obtained.

Workup

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-bf9368f3c5cc400ebb2cbd0b81b4c1fc
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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