Benzyl Alcohol → N-(carbobenzyloxy)amino-3-methoxynaphthalene

Temperatur

80 °C

A solution of 3-methoxy-2-naphthoic acid (3.36 g, 16.6 mmol) and Et3N (2.59 mL, 18.6 mmol) in anh toluene (70 mL) was stirred at room temp. for 15 min., then treated with a solution of DPPA (5.12 g, 18.6 mmol) in toluene (10 mL) via pipette. The resulting mixture was heated at 80° C. for 2 h. After cooling the mixture to room temp., benzyl alcohol (2.06 mL, 20 mmol) was added via syringe. The mixture was then warmed to 80° C. overnight. The resulting mixture was cooled to room temp., quenched with a 10% citric acid solution, and extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography (14% EtOAc/86% hexane) to give 2-(N-(carbobenzyloxy)amino-3-methoxynaphthalene as a pale yellow oil (5.1 g, 100%): 1H-NMR (DMSO-d6) δ 3.89 (s, 3H), 5.17 (s, 2H), 7.27-7.44 (m, 8H), 7.72-7.75 (m, 2H), 8.20 (s, 1H), 8.76 (s, 1H).

1. temperatureAfter cooling the mixture to room temp.
2. temperatureThe mixture was then warmed to 80° C. overnight
3. temperatureThe resulting mixture was cooled to room temp.
4. customquenched with a 10% citric acid solution
5. extractionextracted with EtOAc (2×100 mL)
6. washThe combined organic layers were washed with a saturated NaCl solution
7. dry with materialdried (MgSO4)
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by column chromatography (14% EtOAc/86% hexane)

ORD-Eintrag

ord-fdbf4b2d30004055afc47039e51a280d

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841330B2