Water → HCID 67547185, compound

HRID 490572Notes

Reaction equation

HRID 490572 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]=[N+]=[N-])[CH2:7][N:6]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 14041199HCID 14041199, compound

Product 1

HCID 67547185HCID 67547185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-azido-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester (9) in THF under N2 is added triphenylphosphine and water. The mixture is refluxed with stirring for about 6 h. After removal of THF, the residue is dissolved in Et2O, treated with HCl, stirred for 5 min, and extracted with Et2O. The aqueous solution is then treated with NaHCO3 and extracted, dried and concentrated to afford product 4-amino-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester (10).

Workup

  1. temperatureThe mixture is refluxed
  2. customAfter removal of THF
  3. dissolutionthe residue is dissolved in Et2O
  4. additiontreated with HCl
  5. stirringstirred for 5 min
  6. extractionextracted with Et2O
  7. additionThe aqueous solution is then treated with NaHCO3
  8. extractionextracted
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3805ad0cabab457d8c6c1863a3082ca3
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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