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

HRID 931296Notes

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 (1.25 g, 7.22 mmol) was added to a solution of (R)-ethyl piperidine-3-carboxylate (2.0 g, 10.32 mmol) and triethylamine (2.87 mL, 20.65 mmol) in acetonitrile (25 mL) at room temperature. The reaction mixture was stirred for 3 h at 80° C., then was cooled and was partitioned between ethyl acetate and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 0-25% ethyl acetate in petroleum ether) to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (2 g). MS (ES+APCI) (M+H) 295.0; LCMS retention time 5.246 min (Method R1).

Workup

temperaturewas cooled
customwas partitioned between ethyl acetate and water
dry with materialThe organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude material was purified via column chromatography (100-200 mesh silica gel, 0-25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-1f9a418fb92e41b5bd590f5bbd8c701f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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