Reaktion #2476368

Reaktionsgleichung

4-nitro-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid

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product

Ausbeute 67.7%

4-Amino-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid

Ausbeute 67.7%

Lösungsmittel

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 50° C.
2. 2
   workup.STIRRINGstirred
3. 3
   workup.WAITAfter 2.5 h
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to dryness under reduced pressure
6. 6
   SonstigePurification
7. 7
   SonstigeThe fractions were dried

Vorschrift

To a solution of 4-nitro-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid (0.099 g, 0.22 mmol) in acetic acid (2.00 mL, Fisher) at 20° C. was added zinc (0.185 g, 2.83 mmol, Aldrich). The mixture was stirred for 45 minutes at room temperature. The mixture was heated at 50° C. and stirred. After 2.5 h, the mixture was diluted in acetic acid, filtered and concentrated to dryness under reduced pressure. Purification was by preparative HPLC. The fractions were dried to give 61 mg (52%) product as TFA salt. MS: m/z=432.10 [M+Na]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 7.62-7.74 (m, 3H), 7.36 (dd, J=8.8, 1.8 Hz, 1H), 7.03-7.12 (m, 2H), 4.21-4.32 (m, 1H), 2.20-2.41 (m, 4H), 1.91-2.19 (m, 5H), 1.72 (s, 3H), 1.35-1.51 (m, 4H).

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