Réaction #1244249

Équation de réaction

15

5,7,8-Trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid

N-hydroxysuccinimide

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

→

3

Rendement 68.3%

5,7,8-Trimethoxy-1,4-dihydro-1,4-methanonaphthalene-6-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester

Rendement 68.3%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe resulting reaction mixture
2. 2
   Lavagewashed twice with a 0.01 N HCl solution (50 mL)
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutrePurification

Mode opératoire

To a solution of 15 (0.972 g, 3.52 mmol) in dichloromethane (80 mL) was added N-hydroxysuccinimide (0.547 g, 4.75 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.890 g, 4.64 mmol), and the resulting reaction mixture was stirred under dinitrogen for 15 h. The reaction mixture was diluted with dichloromethane (100 mL), washed twice with a 0.01 N HCl solution (50 mL), dried over sodium sulfate, and concentrated under reduced pressure. Purification was performed using silica gel chromatography (dichloromethane→2:1 ethyl acetate/hexanes) to yield 0.898 g (68%) of 3 as a colorless sticky solid. 1H NMR (300 MHz, CDCl3): δ=2.19-2.27 (m, 2H, CH—CH2—CH), 2.89 (bs, 4H, CH2—CH2), 3.86 (s, 3H, O—CH3), 3.92 (s, 3H, O—CH3), 3.95 (s, 3H, O—CH3), 4.19-4.23 (m, 2H, CH—CH(C)—CH2), 6.78-6.85 (m, 2H, HC═CH); 13C NMR (75 MHz, CDCl3): δ=25.9 (CH2—CH2), 47.7 (CH—CH(C)—CH2), 47.9 (CH—CH(C)—CH2), 61.7 (O—CH3), 62.3 (O—CH3), 62.6 (O—CH3), 68.6 (CH—CH2—CH), 137.7, 142.4 (CH═CH), 143.0 (CH═CH), 144.2, 147.9, 149.6, 149.9, 161.4, 169.1; TLC: Rf=0.42 (2:1 ethyl acetate/hexanes); ESI-MS calcd for C19H19NO7 [M+Na]+: 396.1059. found 396.1069.

Source