1-(Azidomethyl)-3-(phenylmethoxy)benzene → (3-(Benzyloxy)phenyl)methanamine
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[CH2:12][N:13]=[N+]=[N-])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[CH2:12][NH2:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
3-Benzyloxybenzyl azide, as described above in Step H, (5.0 g, 20.9 mmol) was dissolved in dry THF (100 mL) and the solution was cooled to −70° C. Lithium aluminum hydride (31.4 mL of a 1.0 M solution in THF, 31.4 mmol) was added dropwise, then the reaction mixture was warmed to 0° C. and stirred for 30 min. The reaction was quenched with EtOAc (1.2 mL), then water (1.2 mL), then 15% NaOH (1.2 mL), and finally water (3.6 mL). The resulting mixture was filtered, concentrated under reduced pressure and purified by flash column chromatography on silica, eluting with CH2Cl2—3% MeOH—0.3% NH4OH, to yield the titled product as a colorless oil.
Workup
- temperaturethe reaction mixture was warmed to 0° C.
- customThe reaction was quenched with EtOAc (1.2 mL)
- filtrationThe resulting mixture was filtered
- concentrationconcentrated under reduced pressure
- custompurified by flash column chromatography on silica
- washeluting with CH2Cl2—3% MeOH—0.3% NH4OH
Sources & evidence
- ORD record
- ord-d762390aae65447587149f73bedf114f
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06441017B1
Reaction notes
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