Triphenylphosphine → (s)-1-(3-Nitrophenyl)ethanamine
Reaction equation
[N:1]([C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[N+:12]([C:8]1[CH:7]=[C:6]([C@@H:4]([NH2:1])[CH3:5])[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-[(1S)-1-azidoethyl]-3-nitrobenzene (16.5 g, 86 mmol) in a mixture of toluene (325 mL) and water (40 mL) was added triphenylphosphine (44.5 g, 170 mmol) in one portion. The mixture was immediately heated to 80° C. where it was stirred for 3 hours. After this time the mixture was allowed to cool to room temperature, was diluted with ethyl acetate (100 mL), the two phases separated and the organic phase extracted with dilute aqueous hydrochloric acid (2M, 3×100 mL). The acidic extracts were basified to pH>10 with solid potassium hydroxide and were then extracted with dichloromethane (3×100 mL). The organic extracts were washed with brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to give (1S)-1-(3-nitrophenyl)ethanamine (13.1 g, 92%) as a yellow liquid.
Workup
- temperatureto cool to room temperature
- customthe two phases separated
- extractionthe organic phase extracted with dilute aqueous hydrochloric acid (2M, 3×100 mL)
- extractionwere then extracted with dichloromethane (3×100 mL)
- washThe organic extracts were washed with brine (100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-542955f88fd04c07b08b7387ff57eb2a
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029386B2
Reaction notes
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