Triphenylphosphine → (3S)-3-amino-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

HRID 891721Notes

Reaction equation

HRID 891721 reaction equation
[N:1]([C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[NH2:1][C@H:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[CH2:5]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 62649Sodium sulfate decahydrateHCID 86590873(3S)-3-azido-1-(p-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 69543945(3S)-3-amino-1-(p-nitrobenzyloxycarbonyl)pyrrolidineYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (3S)-3-azido-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (3.43 g, 11.6 mmol) (obtained as described in Reference Example 52(3)) in acetonitrile (103 ml) was added triphenylphosphine (3.19 g, 12.2 mmol), and the mixture was stirred in an oil bath (70° C.) for 2 hours. After checking the completion of the reaction, sodium sulfate decahydrate (3.93 g, 12.2 mmol) was added thereto and the reaction mixture was stirred for 5 hours. After checking the completion of the reaction, the reaction mixture was filtered and partitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution. To the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate, and the aqueous layer was extracted with methylene chloride. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was dried under reduced pressure to give (3S)-3-amino-1-(p-nitrobenzyloxycarbonyl)pyrrolidine (2.83 g, yield 92%) as a pale yellow solid.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred for 5 hours
  3. customthe completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. custompartitioned between methylene chloride and 0.1M aqueous hydrogen chloride solution
  6. additionTo the obtained aqueous layer were added methylene chloride and sodium hydrogencarbonate
  7. extractionthe aqueous layer was extracted with methylene chloride
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-a65ebc8640704d41b74952ea48505f04
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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