Water → (S)-b-Amino-4-methylbenzenepropanol

A mixture of lithium aluminum hydride (254 mg, 6.696 mmol) in THF (20 mL) was heated at reflux for 1 h, then cooled in an ice bath. (S)-4-Methylphenylalanine (500 mg, 2.79 mmol) was added portionwise and the resultant mixture was heated at reflux for 14 h. The excess lithium aluminum hydride was decomposed by successive addition of H2O (1 mL), 10% aq. NaOH (10 mL) and H2O (2.5 mL). The mixture was filtered and the solid was washed with THF. The filtrate was concentrated in vacuo and the residue was dissolved in CHCl3 (50 mL), washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford (2S)-2-amino-3-(4-methylphenyl)propan-1-ol as an off-white solid. 1H NMR (CD3OD, 500 MHz) δ 7.13-7.09 (m, 4H), 3.52 (dd, J=10.7, 4.6 Hz, 1H), 3.36 (dd, J=10.7, 6.9 Hz, 1H), 3.04-2.99 (m, 1H), 2.73 (dd, J=13.5, 6.2 Hz, 1H), 2.53 (dd, J=13.5, 7.7 Hz, 1H), 2.30 (s, 3H).

1. temperaturewas heated
2. temperatureat reflux for 1 h
3. temperaturecooled in an ice bath
4. temperatureat reflux for 14 h
5. filtrationThe mixture was filtered
6. washthe solid was washed with THF
7. concentrationThe filtrate was concentrated in vacuo
8. dissolutionthe residue was dissolved in CHCl3 (50 mL)
9. washwashed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORDレコード

ord-7b3a984164b8452d865b2a8311b4a850

出典データセット

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07652049B2