tert-Butanol → tert-Butyl naphthalen-2-ylcarbamate

2-Naphthoic acid (S13-1; 2.5 g, 14.3 mmol) in tert-BuOH (85 mL) and toluene (85 mL) was treated with Et3N (2.3 mL, 16.4 mmol), 3 Å molecular sieves (16.7 g) and diphenyl phosphorylazide (3.5 mL, 16.4 mmol). The reaction mixture was refluxed for 24 h. After cooling to rt, solid was filtered off through Celite and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (75 mL) and washed with 1N aqueous HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL), dried over sodium sulfate and concentrated under reduced pressure. Chromatography (10% EtOAc in hexanes) afforded 2.5 g (71%) of S13-2. 1H NMR (500 MHz, CDCl3) δ 7.99 (s, 1H), 7.72-7.78 (m, 3H), 7.44 (t, J=7.8 Hz, 1H), 7.31-7.38 (m, 2H), 6.61 (br s, 1H), 1.55 (s, 9H); MS (ESI) m/z 244.02 [M+H]+.

1. temperatureThe reaction mixture was refluxed for 24 h
2. filtrationsolid was filtered off through Celite
3. customthe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in EtOAc (75 mL)
5. washwashed with 1N aqueous HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customChromatography (10% EtOAc in hexanes) afforded 2.5 g (71%) of S13-2

ORD-Eintrag

ord-7553088c0ede469093857ad4c9d786d0

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09328114B2