Triethylamine → (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

HRID 931311Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1.C(N(CC)CC)C>C(#N)C>[NH2:8][C:6]1[N:7]=[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

6-Chloro-3-nitropyridin-2-amine (0.8 g, 4.64 mmol) was added to a solution of (R)-ethyl piperidine-3-carboxylate (1.0 g, 5.16 mmol) and triethylamine (1.56 g, 15.48 mmol) in acetonitrile (20 mL) at room temperature. The reaction mixture was stirred at 80° C. for 3 h. The mixture was partitioned between ethyl acetate and water. The organics were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 10-50% ethyl acetate in petroleum ether) to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (1.0 g). MS (ES+) (M+H) 295.22.

Workup

customThe mixture was partitioned between ethyl acetate and water
dry with materialThe organics were dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude material was purified via column chromatography (100-200 mesh silica gel, 10-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-e08cca85406e46048b16c4e490c7c048
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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