HCID 69423771, compound → P-Hydroxynorephedrine

To a suspension of (1S,2R)-2-[2-hydroxy-2-(4-hydroxy-phenyl)-1-methylethyl]isoindol-1,3-dione (1.0 g) in methanol (1.7 mL), methylamine in methanol (40% w/v; 3.5 mL) was added. The mixture was heated under reflux in argon atmosphere for 12 hours. After removing the solvent in vacua, the resulting residue was dissolved in tetrahydrofuran (3 mL) under heating. This solution was cooled and kept at room temperature. After removing the resulting precipitate by filtration, the mother liquor was concentrated in vacua. The resulting residue was recrystallized from ethyl acetate/methanol to obtain (1R, 2S)-2-amino-1-(4-hydroxyphenyl)propan-1-ol (0.30 g: 54% yield, optical purity 100% e.e.).

1. additionwas added
2. temperatureThe mixture was heated
3. temperatureunder reflux in argon atmosphere for 12 hours
4. customAfter removing the solvent in vacua
5. dissolutionthe resulting residue was dissolved in tetrahydrofuran (3 mL)
6. temperatureunder heating
7. temperatureThis solution was cooled
8. customkept at room temperature
9. customAfter removing the resulting precipitate
10. filtrationby filtration
11. concentrationthe mother liquor was concentrated in vacua
12. customThe resulting residue was recrystallized from ethyl acetate/methanol

ORD record

ord-beaef917e26d414ab745017a567d64e0

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07196203B2