Reaktion #472532

Reaktionsgleichung

2-(3-Cyclopropylmethoxy-4-nitro-phenyl)-4-methyl-pentanoic acid cyclopropylmethyl ester

→

2-(4-amino-3-cyclopropylmethoxy-phenyl)-4-methyl-pentanoic acid cyclopropylmethyl ester

Ausbeute 75.0%

Lösungsmittel

AcOH

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 1 h
2. 2
   Temperaturafter cooling the precipitate
3. 3
   Filtrationwas filtered
4. 4
   SonstigeThe solvent was evaporated
5. 5
   workup.ADDITIONwater (150 mL) was added
6. 6
   ExtraktionThe reaction mixture was extracted with EtOAc (3×100 mL)
7. 7
   Waschenthe combined organic phases were washed with water (3×100 mL) and brine (100 mL)
8. 8
   SonstigeDrying of the organic phase
9. 9
   SonstigeThe evaporation of the solvent
10. 10
    Sonstigegave crude product as a brown oil, which
11. 11
    Sonstigewas purified by silica gel gradient column chromatography by use of Heptane-EtOAc

Vorschrift

2-(3-Cyclopropylmethoxy-4-nitro-phenyl)-4-methyl-pentanoic acid cyclopropylmethyl ester (34.0 g, 94.2 mmol) was dissolved in AcOH (300 mL) and water (20 mL). Then, Zn powder (60.0 g, 923 mmol) was added in portions. The reaction mixture was refluxed for 1 h and after cooling the precipitate was filtered. The solvent was evaporated and water (150 mL) was added. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organic phases were washed with water (3×100 mL) and brine (100 mL). Drying of the organic phase was performed with magnesium sulfate. The evaporation of the solvent gave crude product as a brown oil, which was purified by silica gel gradient column chromatography by use of Heptane-EtOAc to give 2-(4-amino-3-cyclopropylmethoxy-phenyl)-4-methyl-pentanoic acid cyclopropylmethyl ester as a yellow oil (23 g, 75%). 1H NMR (300 MHz, CDCl3/TMS): δ 6.73-6.61 (m, 3H), 3.94-3.78 (m, 6H), 3.53 (t, J=7.7 Hz, 1H), 1.94-1.85 (m, 1H), 1.65-1.56 (m, 1H), 1.52-1.43 (m, 1H), 1.28-1.18 (m, 1H), 1.11-1.03 (m, 1H), 0.90 (d, J=6.6 Hz, 6H), 0.64-0.58 (m, 2H), 0.53-0.47 (m, 2H), 0.36-0.33 (m, 2H), 0.24-0.21 (m, 2H); 13C NMR (75 MHz, CDCl3/TMS): δ 174.6, 146.4, 135.3, 129.3, 120.5, 114.6, 111.2, 73.1, 69.0, 49.2, 42.7, 25.8, 22.6, 22.4, 10.4, 9.8, 3.2.

Quelle