N-Nitroso-L-proline → Aminoproline

HRID 569867Notes

Reaction equation

HRID 569867 reaction equation
[N:1]([N:3]1[CH2:10][CH2:9][CH2:8][C@H:4]1[C:5]([OH:7])=[O:6])=O>[Zn].C(O)(=O)C>[NH2:1][N:3]1[CH2:10][CH2:9][CH2:8][C@H:4]1[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 10419304N-Nitroso-L-proline

Product 1

HCID 97357Aminoproline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 10 g. of N-nitroso-L-proline in 500 ml. of 50% acetic acid is cooled in an ice bath and 40 g. of zinc dust is added gradually, with vigorous stirring, at a rate that the temperature of the reaction mixture is maintained below 10°. The addition requires about 15 minutes. The unreacted zinc dust is removed by filtration and the filtrate treated with hydrogen sulfide to precipitate the zinc as zinc sulfide. The precipitated zinc sulfide is removed by filtration and the filtrate evaporated to dryness. The residue is dissolved in 30 ml. of absolute ethanol and the solution allowed to remain overnight at 5°. The N-amino-L-proline, a yellow crystalline solid is removed by filtration and melts at 153°-154° after drying.

Workup

  1. temperatureis maintained below 10°
  2. additionThe addition
  3. customThe unreacted zinc dust is removed by filtration
  4. additionthe filtrate treated with hydrogen sulfide
  5. customto precipitate the zinc as zinc sulfide
  6. customThe precipitated zinc sulfide is removed by filtration
  7. customthe filtrate evaporated to dryness
  8. dissolutionThe residue is dissolved in 30 ml
  9. waitto remain overnight at 5°
  10. customThe N-amino-L-proline, a yellow crystalline solid is removed by filtration and melts at 153°-154°
  11. customafter drying

Sources & evidence

ORD record
ord-42c3b68de38c4dc9bdd9fb528746b4d4
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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