Water → 1-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

HRID 490660Notes

Reaction equation

HRID 490660 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].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>C1COCC1>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H: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 962WaterHCID 11776TriphenylphosphineHCID 147726831-Tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 70099181-tert-butyl 2-methyl (2S,4R)-4-aminopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-azido-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (838 mg, 2.2 mmol), THF (10 ml) and P(Ph)3 (1.15 g, 4.4 mmol) and water (0.08 ml, 4.4 mmol) was refluxed for 6 hours and then concentrated in vacuo. The residue was dissolved in Et2O and treated with HCl (0.1N, 20 ml). The aqueous layer was extracted with Et2O, washed with Na2CO3 (10% aq.), dried over anhydrous MgSO4 and concentrated to afford the amine as colorless oil which was used in next step without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in Et2O
  3. additiontreated with HCl (0.1N, 20 ml)
  4. extractionThe aqueous layer was extracted with Et2O
  5. washwashed with Na2CO3 (10% aq.)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4526118bb63a42d6a4bb20524faaec65
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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