HCID 178418361, compound → 6-Benzyl-1-methyl-5,7-dioxooctahydropyrrolo[3,4-b]pyridine

HRID 36674Notes

Reaction equation

HRID 36674 reaction equation
[I-].[CH2:2]([N:9]=[C:10]([C:12]1[C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=[CH:14][N+:13]=1[CH3:21])[OH:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>COCCO.[Pt]=O>[CH2:2]([N:9]1[C:18](=[O:19])[CH:17]2[CH:12]([N:13]([CH3:21])[CH2:14][CH2:15][CH2:16]2)[C:10]1=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178480315HCID 178480315, compound

Product 1

HCID 150700076-Benzyl-1-methyl-5,7-dioxooctahydropyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 80192-MethoxyethanolSolvent

Procedure

38 g (0.1 mol) of 1-methyl-pyridinium-2,3-dicarboxylic acid N-benzylimide iodide are hydrogenated over 1 g of platinum oxide in 450 ml of glycol monomethyl ether at 30° C. under 70 bar until the uptake of hydrogen has ended (51 hours). The catalyst is then filtered off, the filtrate is concentrated, the residue is taken up in 300 ml of chloroform and the solution is washed 2× with 300 ml of 10% strength sodium carbonate solution each time and with 300 ml of water. After drying over sodium sulphate, it is concentrated. 27 g of an oily residue remain.

Workup

  1. custom(51 hours)
  2. filtrationThe catalyst is then filtered off
  3. concentrationthe filtrate is concentrated
  4. washthe solution is washed 2× with 300 ml of 10% strength sodium carbonate solution each time
  5. dry with materialAfter drying over sodium sulphate, it
  6. concentrationis concentrated

Sources & evidence

ORD record
ord-bc49be5fc1a942c3a3c644164775697d
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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