Reaktion #58515

Reaktionsgleichung

product

2-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[α]pentalene-5-carboxylic acid methyl ester

K2CO3

ACE-Cl

→

titled compound

1,2,3,3a,7,7a-Hexahydro-4-thia-2-aza-cyclopenta[α]pentalene-5-carboxylic acid methyl ester

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled to room temperature
2. 2
   Filtrationfiltered
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe crude oil was dissolved in anhydrous MeOH (2.5 ml)
5. 5
   workup.STIRRINGstirred at room temperature for 3 hours
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigethe product triturated with anhydrous ether
8. 8
   Sonstigeto give a white solid, which
9. 9
   Filtrationwas filtered

Vorschrift

To a solution of the product from step b) (100 mg, 0.32 mmol) in DCE (1.6 ml) was added powdered K2CO3 (176 mg, 1.28 mmol) and ACE-Cl (183 mg, 1.28 mmol). The reaction mixture was heated to 80° C. and stirred for 18 hours. The reaction was cooled to room temperature, filtered, and concentrated in vacuo. The crude oil was dissolved in anhydrous MeOH (2.5 ml) and stirred at room temperature for 3 hours. The solvent was evaporated and the product triturated with anhydrous ether to give a white solid, which was filtered to give the titled compound as its hydrochloride salt: (42.3 mg, 51%), 1H NMR (300 MHz, DMSO, ppm) 2.68 (br d, J=16 Hz, 1H), 2.98-3.06 (m, 2H), 3.19-3.28 (m, 1H), 3.35-3.50 (m, 2H), 3.52-3.62 (m, 1H), 3.80 (s, 3H), 4.00-4.11 (m, 1H), 7.56 (s, 1H), 9.05 (br s, 1H), 9.31 (br s, 1H). MS calculated for C11H13NO2S+H 224, observed 224.

Quelle