Methyl iodide → HCID 2794227, compound

Sodium hydride (60% dispersion in oil: 322 mg, 8.1 mmol) was added to a stirred solution of N-tert-butoxycarbonyl-(S)-1-benzyl-1-aminoethan-2-ol (2.02 g, 8.1 mmol) in dry THF (50 ml) at 0° C. under argon. The mixture was stirred for 10 min. and methyl iodide (3 ml) added. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. Saturated ammonium chloride (80 ml) was added and the mixture extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried over anhydrous sodium sulphate, filtered and concentrated to give a clear oil. The oil was dissolved in DCM (40 ml) and treated with excess trifluoroacetic acid. (6.2 ml) at 0° C. The mixture was allowed to warm up to room temperature and was stirred for 2 h. The mixture was washed with aqueous sodium hydrogen carbonate and brine, and dried over anhydrous sodium sulphate. Filtration and evaporation gave (S)-1-benzyl-2-methoxyethylamine (620 mg, 47%) as a colourless oil.

1. stirringstirred for 1 h
2. extractionthe mixture extracted with ethyl acetate (2×100 ml)
3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a clear oil
7. customat 0° C
8. temperatureto warm up to room temperature
9. stirringwas stirred for 2 h
10. washThe mixture was washed with aqueous sodium hydrogen carbonate and brine
11. dry with materialdried over anhydrous sodium sulphate
12. filtrationFiltration and evaporation

ORD record

ord-a0ca3ee6ab2e477da2a23fbbb3beda6c

Source dataset

uspto-grants-1993_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05180723