Reaktion #1859541

Reaktionsgleichung

methyl-(1R,2S)-1-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-ylcarbamoyl)-2-methylcyclopropylcarbamate

piperidine

Acetic acid

→

(1R,2S)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one

Ausbeute 72.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe solution was washed with water
2. 2
   Extraktionextracted twice with ethyl acetate
3. 3
   Waschenwashed with brine
4. 4
   Einengenconcentrated
5. 5
   workup.STIRRINGthe solution was stirred at 90° C
6. 6
   Einengen3 h before being concentrated with celite
7. 7
   Sonstigepurified by column chromatography

Vorschrift

A round bottomed flask was charged with 9H-fluoren-9-yl)methyl-(1R,2S)-1-(3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-ylcarbamoyl)-2-methylcyclopropylcarbamate (225 mg, 0.385 mmol) and a stir bar. DMF (16 mL, 0.02 M) was added, followed by piperidine (4 mL, 40.4 mmol), and the solution was stirred at room temperature 15 min. The solution was washed with water, extracted twice with ethyl acetate, washed with brine, and concentrated before being taken up in ethanol (25 mL). Acetic acid (12.5 mL, 218 mmol) was added, and the solution was stirred at 90° C. 3 h before being concentrated with celite and purified by column chromatography to give (1R,2S)-5′-(4-chlorophenyl)-2,6′,7′-trimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one (Compound 218) as a light yellow amorphous solid (96 mg). LRMS (M+H)+: 345 m/z.

Quelle