1-(3-Nitropyridin-2-yl)piperidin-4-one → 2-(4-Methylene-1-piperidyl)-3-nitropyridine

HRID 2040842Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[N+:6]([C:9]1[C:10]([N:15]2CCC(=O)[CH2:17][CH2:16]2)=[N:11][CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:4]=[C:3]1[CH2:17][CH2:16][N:15]([C:10]2[C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:1][CH2:2]1

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyllithium in hexanes (2.5 M, 4.93 mL, 12.3 mmol) was added dropwise over 10 min. into a suspension of 98% methyltriphenylphosphonium bromide (4.65 g, 12.8 mmol) in 40 mL of THF stirred at −70° C. After 0.5 h, a solution of 1-(3-nitro-2-pyridyl)-4-oxopiperidine (2 g, 8.5 mmol) in 16 mL of THF was added and the reaction mixture was allowed to warm up to r.t. After overnight resting, the mixture was quenched with an aqueous saturated solution of NH4Cl, extracted with EtOAc, dried over Na2SO4, evaporated to dryness in vacuo. The crude product was purified by automated flash chromatography (SP1®TM-Biotage) eluting with a Petroleum Ether-EtOAc gradient from 1:0 to 9:1 yielding 1.23 g of the title compound as yellow solid.

Workup

temperatureto warm up to r.t
waitAfter overnight resting
customthe mixture was quenched with an aqueous saturated solution of NH4Cl
extractionextracted with EtOAc
dry with materialdried over Na2SO4
customevaporated to dryness in vacuo
customThe crude product was purified by automated flash chromatography (SP1®TM-Biotage)
washeluting with a Petroleum Ether-EtOAc gradient from 1:0 to 9:1 yielding 1.23 g of the title compound as yellow solid

Sources & evidence

ORD record: ord-111faa23f5ee4c8ea48bbb529abc5a2f
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580962B2

Reaction notes

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