Triphenylphosphine → (3S)-(+)-1-Benzyl-3-aminopyrrolidine

HRID 2375449Notes

Reaction equation

HRID 2375449 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]=[N+]=[N-])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 10821988HCID 10821988, compound

Product 1

HCID 1519353(3S)-(+)-1-Benzyl-3-aminopyrrolidineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (3S)-1-benzyl-3-azidopyrrolidine (0.9 g, 4.5 mM) was dissolved in a mixture of tetrahydrofuran (36.0 ml) and water (7.0 ml). To it, triphenylphosphine (2.3 g, 8.9 mM) was added and the reaction mixture was refluxed for 7 hours. The reaction mixture was cooled to room temperature and tetrahydrofuran was evaporated under vacuum. The residue was taken in water (50.0 ml) and the pH was adjusted to about 2 and washed with chloroform. The pH of the aqueous solution was adjusted to about 12-13 with 1N sodium hydroxide and extracted with chloroform. The chloroform layer was washed with water and brine solution. It was further dried over anhydrous sodium sulphate and concentrated to give the title compound. Yield=62% (0.5 g, 2.8 mM).

Workup

  1. temperaturethe reaction mixture was refluxed for 7 hours
  2. customtetrahydrofuran was evaporated under vacuum
  3. washwashed with chloroform
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water and brine solution
  6. dry with materialIt was further dried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fcec55e52c60487bb031edd7ac6006e7
Source dataset
uspto-grants-2008_12
Patent number
US07465751B2

Reaction notes

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