Benzyl Alcohol → HCID 59999814, Verbindung

Triethylamine (1.2 ml, 8.9 mmol) followed by diphenylphosphoryl azide (1.6 ml, 7.4 mmol) was added to a solution of 4-tert-butyl hydrogen 2-(4-chlorophenylpropyl)succinate (WO 9504033 intermediate 2f) (2.4 g, 7.4 mmol) in toluene (250 ml), and the solution stirred at room temperature for 30 minutes, then under reflux for a further 3 hours. The mixture was cooled to 50° C., benzyl alcohol (2.3 ml, 22.3 mmol) added, and the reaction heated under reflux for 18 hours. The cooled mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate (125 ml). This solution was washed with saturated ammonium chloride solution (100 ml), brine (100 ml) and water (100 ml), then dried (MgSO4) and concentrated under reduced pressure. The product was purified by column chromatography on silica gel using ethyl acetate:pentane (6:94) as eluant to afford the title compound as a colourless oil 1.59 g; 1H NMR (CDCl3, 400 MHz) δ: 1.41 (s, 9H), 1.46–1.70 (m, 4H), 2.40 (m, 2H), 2.58 (m, 2H), 3.98 (m, 1H), 5.10 (s, 2H), 5.20 (d, 1H), 7.05 (d, 2H), 7.22 (m, 3H), 7.32 (m, 4H); LRMS: m/z (ES+) 454 [MNa+].

1. temperatureunder reflux for a further 3 hours
2. temperatureThe mixture was cooled to 50° C.
3. temperaturethe reaction heated
4. temperatureunder reflux for 18 hours
5. concentrationThe cooled mixture was concentrated under reduced pressure
6. dissolutionthe residue dissolved in ethyl acetate (125 ml)
7. washThis solution was washed with saturated ammonium chloride solution (100 ml), brine (100 ml) and water (100 ml)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated under reduced pressure
10. customThe product was purified by column chromatography on silica gel

ORD-Eintrag

ord-4e3c141ec2224ec79bea93d9c1e611b9

Quelldatensatz

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07045653B2