반응 #156868

반응 방정식

triphenyl phosphite

Methyl 6-(2-(2-tert-butoxy-2-oxoethyl)pyrrolidin-1-yl)-5-nitronicotinate

→

methyl 6-oxo-6,7,7a,8,9,10-hexahydro-5H-pyrido[3,2-b]pyrrolo[1,2-d][1,4]diazepine-3-carboxylate

수율 72.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered through a short plug of celite
2. 2
   세척the plug and precipitate were washed well with dichloromethane (30 mL)
3. 3
   농축The combined filtrates were concentrated in vacuo
4. 4
   workup.DISSOLUTIONdissolved in AcOH (7 mL)
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was crystallized with ethyl ether (20 mL)
7. 7
   기타sonicated until a fine suspension
8. 8
   기타was obtained The precipitate
9. 9
   여과was filtered off
10. 10
    기타dried in vacuum

실험 절차

Methyl 6-(2-(2-tert-butoxy-2-oxoethyl)pyrrolidin-1-yl)-5-nitronicotinate (1.79 g, 4.90 mmol) was dissolved in dichloromethane (Volume: 24.49 ml) and to this solution was added triphenyl phosphite (0.015 g, 0.049 mmol), ammonium metavanadate (0.034 g, 0.294 mmol) and Pt/C (5% wt.) (0.191 g, 0.049 mmol). The reaction mixture was hydrogenated at 100 psi at 25° C. for 3 h. The reaction mixture was filtered through a short plug of celite and the plug and precipitate were washed well with dichloromethane (30 mL). The combined filtrates were concentrated in vacuo and dissolved in AcOH (7 mL). This solution was heated to 90° C. for 10 min and concentrated in vacuo. The residue was crystallized with ethyl ether (20 mL) and sonicated until a fine suspension was obtained The precipitate was filtered off and dried in vacuum to afford methyl 6-oxo-6,7,7a,8,9,10-hexahydro-5H-pyrido[3,2-b]pyrrolo[1,2-d][1,4]diazepine-3-carboxylate (0.927 g, 3.55 mmol, 72.4% yield) as a light pink solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.71 (m, 1 H) 1.74-1.89 (m, 1 H) 1.89-1.99 (m, 1 H) 2.19 (d, J=5.81 Hz, 1 H) 2.59 (dd, J=14.78, 1.64 Hz, 1 H) 2.77 (dd, J=14.78, 9.98 Hz, 1 H) 3.56-3.67 (m, 1 H) 3.67-3.76 (m, 1 H) 3.78 (s, 3 H) 3.99 (td, J=9.85, 5.56 Hz, 1 H) 7.64 (d, J=2.02 Hz, 1 H) 8.40 (d, J=2.02 Hz, 1 H) 9.73 (d, 1 H) [M+H] calc'd for C13H15N3O3, 261; found, 261.

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