Water → (R)-1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylic acid

HRID 931198Notes

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]([OH:16])=[O:15])[CH2:9]2)[CH:5]=[CH:4][C:3]=1[N+:17]([O-])=O.O.C([O-])=O.[NH4+]>CN(C)C=O.[Zn]>[NH2:17][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]2)=[N:7][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid in N,N-dimethylformamide (91 mL) was added water (9.8 mL), ammonium formate (3.85 g, 61.25 mmol), and active zinc dust (2.1 g, 30.6 mmol) under a nitrogen atmosphere. The reaction mixture was stirred at 45° C. for 16 h. The mixture was filtered and concentrated under reduced pressure to afford (R)-1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylic acid which was used without further purification.

Workup

filtrationThe mixture was filtered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ae3353a7eb8f488eae9e783cb112bfd4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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