N-(2-phenylethyl)hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a THF solution (1.1 mL, 1.0 M) of BH3-THF (1.1 mmol) was added dropwise a THF solution (2.2 mL) of trans-β-nitrostyrene (160.0 mg, 1.1 mmol) at 0° C. under nitrogen atmosphere. NaBH4 (3.3 mg, 0.087 mmol) was added, and the mixture was stirred for 20 minutes at room temperature. Water (5 mL) was added at 0° C., and then the solution was made acidic by adding 2M HCl aqueous solution, and the solution was stirred for 4 hr at 65° C. The reaction mixture was extracted with ethyl acetate, and the aqueous layer was further extracted with ethyl acetate after the addition of 15% NaOH aqueous solution and NaCl. The organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flush column chromatography (chloroform:methanol=1:0→10:1) to obtain the objective substance (62.7 mg, 43%) as white crystals. the solution was stirred for 4 hr at 65° C The reaction mixture was extracted with ethyl acetate the aqueous layer was further extracted with ethyl acetate after the addition of 15% NaOH aqueous solution and NaCl The organic layers were dried over anhydrous magnesium sulfate filtered evaporated The residue was purified by flush column chromatography (chloroform:methanol=1:0→10:1) to obtain the objective substance (62.7 mg, 43%) as white crystals