1,4,5,6-tetrahydro-Cyclopenta[b]pyrrole-2-carboxylic acid ethyl ester synthesis
- Product Name:1,4,5,6-tetrahydro-Cyclopenta[b]pyrrole-2-carboxylic acid ethyl ester
- CAS Number:124455-77-2
- Molecular formula:C10H13NO2
- Molecular Weight:179.22
Yield:124455-77-2 34%
Reaction Conditions:
Stage #1: 1-(N-morpholino)cyclopent-1-ene;ethyl 3-bromo-2-(hydroxyimino)propanoate in toluene at 20; for 3.5 h;
Stage #2: with triiron dodecarbonyl;trifluoroacetic acid in toluene at 130; for 3 h;
Steps:
19.1
Compound 54 (4.38 g, 28.6 mmol) was dissolved in toluene (80 mL), the compound 3(3 g, 14.3 mmol) was added to the solution, and the resulting mixture was stirred at room temperature for 3.5 hours. Water (40 mL) was added to the mixture, and the organic layer was dried over anhydrous magnesium sulfate. Fe3(CO)12 (10.80g, 21.4 mmol) and trifluoroacetic acid (3.3 mL, 42.9 mmol) were added to the organic layer at room temperature, the resulting mixture was stirred at 130 °C for 3 hours. After cooling to room temperature, the reaction mixture was filtered through Celite pad, the filtrated was concentrated in vacuo. The obtained residue was purified by silicagel column chromatography (hexane-ethyl acetate) to give Compound 55 (863.3 mg, Yield 34 %). 1H-NMR(DMSO-d6, / TMS)δppm: 11.4 (s, 1H), 6.48 (s, 1H), 4.18 (q, J = 7.2Hz, 2H), 2.61 (t, J = 6.9Hz, 2H), 2.50 (t, J = 6.6Hz, 2H), 2.32 (tt, J = 6.6, 6.9Hz, 2H), 1.24 (t, J = 7.2Hz, 3H).
References:
EP2460794,2012,A1 Location in patent:Page/Page column 80-81
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