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Itaconic acid → 1-Cyclohexyl-5-oxopyrrolidine-3-carboxylic acid

HRID 58554
Notes
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Reaction equation

HRID 58554 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]=[C:9]([CH2:13][C:14](O)=[O:15])[C:10]([OH:12])=[O:11].[OH-].[Na+]>O>[CH:1]1([N:7]2[C:14](=[O:15])[CH2:13][CH:9]([C:10]([OH:12])=[O:11])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 811Itaconic acidHCID 7965CyclohexylamineHCID 14798Sodium Hydroxide

Product 1

HCID 2385461-Cyclohexyl-5-oxopyrrolidine-3-carboxylic acidYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of cyclohexanamine (3.70 mL; 31.94 mmol) and 2-methylenesuccinic acid (5.04 g; 41.62 mmol) in water (10 mL) was heated in a sealed tube at 110° C. for 21 hours. After cooling to room temperature, 6N NaOH (10 mL) was added and the resulting precipitate was filtered off. The filtrate was acidified with 6N hydrochloric acid to pH 1 and the resulting precipitate was filtered, washed with water, and dried to yield 3.92 g (58%) of 1-cyclohexyl-5-oxopyrrolidine-3-carboxylic acid as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was filtered off
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f89a7a3e2ec1406fb3da65e56c726d6c
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434722B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes