2,3-Dihydroxybutanedioic Acid → 1-Decyl-3,4-dihydroxypyrrolidine-2,5-dione

HRID 2304751Notes

Reaction equation

HRID 2304751 reaction equation
[CH2:1]([NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:12](O)(=[O:20])[CH:13]([CH:15]([C:17](O)=[O:18])[OH:16])[OH:14]>C1(C)C=CC=CC=1>[CH2:1]([N:11]1[C:17](=[O:18])[CH:15]([OH:16])[CH:13]([OH:14])[C:12]1=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic Acid2×HCID 8916Decylamine2×

Product 1

HCID 229615151-Decyl-3,4-dihydroxypyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

N-Decyl DL-tartarimide was prepared by the reaction of n-decyl amine with DL-tartaric acid. DL-Tartaric acid (10.143 g, 67.579 mmole) and toluene (17.332 g) were weighed into a 250 mL 3-necked round-bottomed flask equipped with a teflon-coated magnetic stir bar. A Claisen adapter was placed in the center neck, a Dean-Stark trap was placed on top of the Claisen adapter, and a condenser was placed in the neck of the Dean-Stark trap. A nitrogen inlet adapter was placed on the condenser. In the left neck was placed a pressure-equalizing addition funnel containing n-decyl amine (10.630 g, 67.578 mmole) and toluene (6.257 g, added to ensure complete transfer of the amine). In the right neck was placed a rubber septum which held a thermocouple. The apparatus was purged with nitrogen for 10-15 minutes and then heated to ˜100° C.

Workup

  1. customequipped with a teflon-coated magnetic stir bar
  2. customA nitrogen inlet adapter was placed on the condenser
  3. additiona pressure-equalizing addition funnel
  4. additionadded
  5. customThe apparatus was purged with nitrogen for 10-15 minutes

Sources & evidence

ORD record
ord-328ad3d7a1e64374a406f4623db09107
Source dataset
uspto-grants-2002_08
Patent number
US06437009B1

Reaction notes

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