Triphenylphosphine → [4-(4-Aminobutyl)phenyl]acetic acid
Reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]=[N+]=[N-])=[CH:7][CH:6]=1)([OH:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1>[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1)([OH:3])=[O:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Azide 7 (1.7 g, 7.2 mmol) and triphenylphosphine (1.9 g, 7.2 mmol) were dissolved in a 10% solution of water in THF (66 mL) and stirred overnight at 25° C. Then more triphenylphosphine (0.8 g, 3 mmol) was added and the heating was continued at 60° C. (oil bath) for 6 h. The solvent was removed under reduced pressure and the residue was treated with 2M HCl (100 mL) and extracted with ethyl acetate (2×50 mL). The water fraction was collected and ammonium hydroxide was added until the pH reached approximately 13. The mixture was extracted with ethyl acetate (2×100 mL) then the organic fraction was washed with brine, water and dried with sodium sulfate. Ethyl acetate was removed under reduced pressure to give 0.8 g (53%) of amine 8.
Workup
- customwas continued at 60° C.
- customfor 6 h
- customThe solvent was removed under reduced pressure
- additionthe residue was treated with 2M HCl (100 mL)
- extractionextracted with ethyl acetate (2×50 mL)
- customThe water fraction was collected
- additionammonium hydroxide was added until the pH
- extractionThe mixture was extracted with ethyl acetate (2×100 mL)
- washthe organic fraction was washed with brine, water
- dry with materialdried with sodium sulfate
- customEthyl acetate was removed under reduced pressure
Sources & evidence
- ORD record
- ord-64ebc3fc6a3d43e28ca14a791fae0024
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858615B2
Reaction notes
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