Benzylamine → tert-butyl(1R)-1-benzyl-2-(benzylamino)ethylcarbamate

Temperature

100 °C

The product from Example 70A (1.77 g, 7.6 mmol) in toluene (15 mL) was treated with benzylamine (8.4 mL, 76 mmol) in a sealed tube. After heating at 100° C. for 4 days, the mixture was allowed to cool to ambient temperature and was concentrated. The residue was dissolved in ethyl acetate (50 mL) and the ethyl acetate was washed with 10% citric acid (2×50 mL) and brine (50 mL). A precipitate fell out of the brine. The brine wash was filtered and the filter cake dissolved in ethyl acetate. All the ethyl acetate solutions were combined, wash with aqueous 10% NaHCO3 (2×100 mL), brine, (100 mL), dried over magnesium sulfate, filtered, and the filtrate was concentrated to provide the title compound as a white solid (2.58 g). 1H NMR (CDCl3) δ 7.49-7.12 (m, 10H), 4.98 (m, 1H), 4.00 (br s, 1H), 3.87 (q, 2H), 2.94-2.73 (m, 5H); MS (ESI+) m/z 341 (M+H)+.

1. temperatureto cool to ambient temperature
2. concentrationwas concentrated
3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
4. washthe ethyl acetate was washed with 10% citric acid (2×50 mL) and brine (50 mL)
5. washThe brine wash
6. filtrationwas filtered
7. dissolutionthe filter cake dissolved in ethyl acetate
8. washwash with aqueous 10% NaHCO3 (2×100 mL), brine, (100 mL)
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationthe filtrate was concentrated

ORD record

ord-6077713af2a845dda595c1f8add8f0e1

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524753B2