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

HRID 931244
Notes
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Reaction equation

HRID 931244 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:19]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:19][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:9]2)=[N:7][C:2]=1[NH2:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 131735158(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 131735159(R)-ethyl 1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylateYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (300 mg, 1.019 mmol) in ethanol (15 mL) was added a suspension of 10% palladium-on-carbon (200 mg) in ethanol under nitrogen atmosphere. The mixture was hydrogenated using a hydrogen balloon for 2 h at room temperature then was filtered through a pad of Celite. The filtrate was concentrated to afford (R)-ethyl 1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylate (250 mg) which was used without further purification.

Workup

  1. customfor 2 h
  2. customat room temperature
  3. filtrationthen was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2b7ac2ac477e4519be0bc0117ff8f79a
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296745B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes