Dimethyl 4-(3-methoxy-3-oxopropyl)-4-nitroheptanedioate → HCID 13646943, compound

HRID 280578Notes

Reaction equation

HRID 280578 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]([CH2:16][CH2:17][C:18]([O:20]C)=[O:19])([N+:13]([O-])=O)[CH2:7][CH2:8][C:9](OC)=[O:10]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:7][CH2:8][C:9](=[O:10])[NH:13]1

Participants

4

Reactant 1

HCID 10860141Dimethyl 4-(3-methoxy-3-oxopropyl)-4-nitroheptanedioate

Product 1

HCID 13646943HCID 13646943, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 160 g of crude γ-carbomethoxyethyl-γ-nitropimelic acid dimethyl ester in 800 ml of methanol is hydrogenated at approximately 50 psi using 2 g of 20% Pd/C as catalyst. The resulting slurry is filtered to remove the catalyst and the filtrate is concentrated at reduced pressure to yield crude 5-oxo-2,2-pyrrolidinedipropanoic acid methyl ester and 5-oxo-2,2-pyrrolidinedipropionic acid monomethyl ester. The crude esters are dissolved in 100 ml of methanol and 100 ml of water and are treated with 120 g of 50% sodium hydroxide solution. The reaction mixture is stirred and is heated to 100° C. with distillation of methanol.

Workup

  1. filtrationThe resulting slurry is filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated at reduced pressure

Sources & evidence

ORD record
ord-8beef771d9bd4c0680d18c1bba224283
Source dataset
uspto-grants-1986_05
Patent number
US04590204

Reaction notes

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