Réaction #1973913

Équation de réaction

8-chloro-9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester

triethylamine

→

9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester

Rendement 88.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction was filtered through a pad of celite
2. 2
   Lavagewashed with methanol
3. 3
   Autrethe solvent was removed in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (300 mL)
5. 5
   Lavagewashed with 10% aqueous potassium carbonate (200 mL)
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

8-chloro-9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (15) (5.3 g, 15.0 mmol) was dissolved in methanol (180 mL) and triethylamine (1.8 g, 18.0 mmol, 2.5 mL) and 10% Pd/C (2 g in methanol (20 mL)) were added. The mixture was placed on the Parr hydrogenator and shaken for 18 h under a hydrogen atmosphere. The reaction was filtered through a pad of celite, washed with methanol and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL) and washed with 10% aqueous potassium carbonate (200 mL), dried over magnesium sulfate and concentrated in vacuo to give 4.2 g (88%) of 9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (16) as a light brown solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 14.3, 20.6, 21.8, 27.6, 40.3, 43.3 (d, JCF=23 Hz), 54.9, 60.1, 82.0 d, JCF=165 Hz), 99.8, 102.1, 107.3, 117.2, 121.8, 134.9, 137.6, 153.8, and 176.0.

Source