Reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[C:19]([N+:20]([O-])=O)=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[O:2]=[C:3]1[NH:20][C:19]2[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=[N:11][C:10]=2[N:6]2[CH2:7][CH2:8][CH2:9][C@@H:5]12Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate (1.45 g, 46.9 mmol) and triphenyl phosphite (5.00 mg, 0.0161 mmol) were dissolved in dichloromethane (12 mL). Ammonium metavanadate (50 mg, 0.427 mmol) and Pt/C (5% wt., 200 mg) were added and the reaction mixture was stirred under hydrogen (80 psi) for 5 h. The reaction mixture was filtered through a small plug of celite and the precipitate was washed multiple times with hot dichloromethane until it was free from white precipitate. The filtrate was concentrated in vacuo and crystallized with ethyl ether (15 mL). The resulting solid was filtered off and dried in vacuum to afford the title compound as an off-white solid (0.930 g, 80%). [M+H] calc'd for C12H13N3O3, 248. found, 248.
Workup
- filtrationThe reaction mixture was filtered through a small plug of celite
- washthe precipitate was washed multiple times with hot dichloromethane until it
- concentrationThe filtrate was concentrated in vacuo
- customcrystallized with ethyl ether (15 mL)
- filtrationThe resulting solid was filtered off
- customdried in vacuum
Sources & evidence
- ORD record
- ord-2e3ea43107bf4c138b0db96ff4a9f7d3
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187497B2
Linked notes
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