Water → HCID 58056236, compound

HRID 1773595Notes

Reaction equation

HRID 1773595 reaction equation
[N:1]([CH:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[CH2:7]1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([CH:4]([NH2:1])[CH3:5])[CH2:7]2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58056181HCID 58056181, compound

Product 1

HCID 58056236HCID 58056236, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-(1-azido-ethyl)-1-(4-chloro-2-nitro-phenyl)-pyrrolidine (214 mg, 0.7 mmol), triphenylphosphine (500 mg) and water (0.171 mL) in tetrahydrofuran (20 mL) was heated at 50° C. overnight. The resulting mixture was evaporated under reduced pressure; the residue was diluted with ethyl acetate, washed twice with water and once with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (DCM/MeOH) to give 127 mg (65% yield) of 1-[1-(4-chloro-2-nitro-phenyl)-pyrrolidin-3-yl]-ethylamine.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed twice with water and once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-96c09f4c499647c0bc57bf20bab807d0
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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