Tetrahydrofuran → 1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

HRID 490585Notes

Reaction equation

HRID 490585 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]=[N+]=[N-])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4].C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 147726831-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, THF and PPh3 and water is refluxed for about 6 hours and then concentrated. The residue is dissolved in Et2O and treated with HCl. The aqueous layer is extracted, washed, dried and concentrated to afford 4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (32).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in Et2O
  3. additiontreated with HCl
  4. extractionThe aqueous layer is extracted
  5. washwashed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca3423770c7d4ee4912b5b9c85140986
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

Loading…