Methyl 6-chloro-5-nitronicotinate → (S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate

HRID 2077822

Reaction equation

HRID 2077822 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH3:9])=[O:7].Cl[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1>CCOC(C)=O>[CH3:9][O:8][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][N:1]1[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=[O:7]

Participants

4

Reactant 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 853477Methyl L-prolinate

Product 1

HCID 58324504(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinateYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

(S)-Methyl pyrrolidine-2-carboxylate (6.56 g, 50.8 mmol) was added to methyl 6-chloro-5-nitronicotinate (5.00 g, 23.1 mmol) and the reaction mixture was stirred at 90° C. for 10 min (exothermic reaction). It as cooled to room temperature, diluted with EtOAc (10 mL) and purified using flash column chromatography on silica gel (20-30% EtOAc in hexanes) to afford the title compound as a yellow oil (6.70 g, 94%). [M+H] calc'd for C13H15N3O6, 310; found, 310.

Workup

  1. custom(exothermic reaction)
  2. temperatureIt as cooled to room temperature
  3. custompurified

Sources & evidence

ORD record
ord-6fff8342291449c181140509215598f3
Source dataset
uspto-grants-2011_04
Patent number
US07928105B2

Linked notes

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