4,4-Dimethylpyrrolidine-2-carboxylic acid → 4,4-Dimethyl-1-nitrosopyrrolidine-2-carboxylic acid

HRID 1158897Notes

Reaction equation

HRID 1158897 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][NH:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[N:11]([O-])=[O:12].[Na+]>CC(O)=O.O>[CH3:1][C:2]1([CH3:10])[CH2:6][N:5]([N:11]=[O:12])[CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 2866424,4-Dimethylpyrrolidine-2-carboxylic acidHCID 23668193Sodium Nitrite

Product 1

HCID 219413404,4-Dimethyl-1-nitrosopyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of 37.5 g of the crude 4,4-dimethylpyrrolidine-2-carboxylic acid in 420 mL of AcOH was added a solution of 13.3 g (0.19 mol) of NaNO2 in 210 mL of water over 15 min at room temperature and stirred for 3 h. The solution was concentrated under reduced pressure. Acetone (250 mL) was added to the residue and the precipitate was filtered off, and the solution was concentrated under reduced pressure to dryness and crude 4,4-dimethyl-1-nitrosopyrrolidine-2-carboxylic acid was obtained as brown oil.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionAcetone (250 mL) was added to the residue
  3. filtrationthe precipitate was filtered off
  4. concentrationthe solution was concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-4b852bac36694b61ab56061f9a7006d4
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

Loading…