1-(Azidomethyl)-3-(phenylmethoxy)benzene → (3-(Benzyloxy)phenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence