Hydrochloric Acid → 1-Hydroxylamino-2-phenylethane

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.

1. stirringthe solution was stirred for 4 hr at 65° C
2. extractionThe reaction mixture was extracted with ethyl acetate
3. extractionthe aqueous layer was further extracted with ethyl acetate
4. additionafter the addition of 15% NaOH aqueous solution and NaCl
5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified
9. customby flush column chromatography (chloroform:methanol=1:0→10:1)
10. customto obtain the objective substance (62.7 mg, 43%) as white crystals

ORD record

ord-5c7bbfe7a34d44e690fa30cc99c3d361

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524980B2