Reaktion #642450

Reaktionsgleichung

hydrochloric acid

3-[5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic acid ethyl ester

sodium hydroxide

→

title compound

Ausbeute 74.6%

3-[5-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic Acid

Ausbeute 74.6%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewere removed in vacuo
2. 2
   Extraktionthe aqueous residues were extracted with DCM (3×5 mL)
3. 3
   TrocknenThe combined organic phases were dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   SonstigeThe resulting solid was purified by preparative HPLC
7. 7
   Sonstigedried in vacuo at 50° C.

Vorschrift

To a solution of 3-[5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic acid ethyl ester (80 mg, 0.2 mmol) in ethanol (2 mL) was added 1N aqueous sodium hydroxide solution (2 mL), and the resulting solution stirred for 2 h. The solution was acidified with 1N hydrochloric acid solution before the organic volatiles were removed in vacuo, and the aqueous residues were extracted with DCM (3×5 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. The resulting solid was purified by preparative HPLC, dried in vacuo at 50° C. affording 55 mg (74%) of the title compound as a solid. MS-ESI m/z 369; 1H NMR (400 MHz, DMSO-d6) δ 0.94 (d, 3H), 1.04 (d, 3H), 1.13-1.17 (m, 4H), 1.28-1.38 (m, 2H), 1.43-1.45 (m, 1H), 1.60-1.63 (m, 1H), 1.75-1.79 (m, 1H), 2.24-2.32 and 3.25-3.26 (m, 1H), 2.74 (t, 2H), 3.27-3.35 (m) and 3.62-3.65 (m), 1H), 4.08-4.10 and 4.62-4.63 (m, 1H), 4.39 (t, 2H), 6.47-6.48 (m, 1H), 7.17-7.23 (m, 3H), 7.70 (d, 1H).

Quelle