Ammonium Sulfate → 4,4-Dimethylpyrrolidine-2-carboxylic acid

HRID 2216599Notes

Reaction equation

HRID 2216599 reaction equation
Cl[CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][NH:4][C:3]1=[O:10].S([O-])([O-])(=O)=[O:12].[NH4+].[NH4+]>O>[CH3:9][C:6]1([CH3:8])[CH2:5][NH:4][CH:2]([C:3]([OH:10])=[O:12])[CH2:7]1

Participants

4

Reactant 2

HCID 6097028Ammonium SulfateHCID 219413793-Chloro-5,5-dimethylpiperidin-2-one

Product 1

HCID 2866424,4-Dimethylpyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 20.4 g (0.13 mol) of 3-chloro-5,5-dimethyl-2-piperidone and 45.2 g (0.14 mol) of Ba(OH)3-8H2O in 252 mL of water was heated in a Parr apparatus at 150° C. for 6 h. Then, 18.6 g (0.14 mol) of ammonium sulphate were added. The precipitate was filtered off, and the solution was concentrated under reduced pressure to dryness. Crude 4,4-dimethylpyrrolidine-2-carboxylic acid was obtained as a white solid (37.5 g). (J. Med. Chem., 20, 1176 (1977), EP 0 447 704 A1, page 17)

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe solution was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-2bde3c7c81674c85943c311b1610dae4
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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