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

HRID 931243Notes

Reaction equation

HRID 931243 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[NH2:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15](Cl)[N:14]=1.C(N(CC)CC)C>CS(C)=O>[NH2:12][C:13]1[N:14]=[C:15]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]2)[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 131735158(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylateYield 93.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (R)-ethyl piperidine-3-carboxylate (1 g, 6.33 mmol) in dimethylsulfoxide (15 mL) were added 2-amino-3-nitro-6-chloropyridine (1.098 g, 6.33 mmol) and triethylamine (1.921 g, 18.99 mmol) at room temperature. The mixture was heated to 100° C. for 18 h, then was poured into ice water and extracted with ethyl acetate. The organic layer was dried, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (100-200 mesh silica, 30% ethyl acetate in petroleum ether) to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (650 mg, 93.5%). MS (ES+APCI) (M+H) 295.1; LCMS retention time 2.832 min (Method G).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified via flash chromatography (100-200 mesh silica, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-77b90b466a7f41e3b09a84a8102f3920
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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