L-Proline, ethyl ester → (S)-ethyl 1-(5-bromo-3-nitropyridin-2-yl)pyrrolidine-2-carboxylate

HRID 69715

Reaction equation

HRID 69715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][C@H:13]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 79888L-Proline, ethyl esterHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 58324356(S)-ethyl 1-(5-bromo-3-nitropyridin-2-yl)pyrrolidine-2-carboxylateYield 98%

Conditions

Temperature
90 °C

Procedure

5-bromo-2-chloro-3-nitropyridine (5.94 g, 25 mmol) and (S)-ethyl pyrrolidine-2-carboxylate (7.52 g, 52.5 mmol) were combined and stirred at 90° C. for 10 min in a closed vial. The crude material was purified by flash column chromatography (20-30% EtOAc in hexanes to afford (S)-ethyl 1-(5-bromo-3-nitropyridin-2-yl)pyrrolidine-2-carboxylate (8.43 g, 24.49 mmol, 98% yield) as a yellow viscous oil. [M+H] calc'd for C12H14BrN3O4, 344; found, 344.

Workup

  1. customThe crude material was purified by flash column chromatography (20-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-bb4a549c5f6f4e35b9cca064c95a6699
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Linked notes

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