Diisopropylethylamine → (R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid

HRID 931193Notes

Reaction equation

HRID 931193 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]([OH:20])=[O:19])[CH2:13]1.C(N(C(C)C)CC)(C)C>>[NH2:8][C:6]1[N:7]=[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([OH:20])=[O:19])[CH2:13]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 1796510(-)-Nipecotic acidHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 89853836(R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid

Conditions

Temperature
80 °C

Procedure

A solution of 6-chloro-3-nitropyridin-2-amine (0.175 M, 35 mL, 6.125 mmol) was added to (R)-piperidine-3-carboxylic acid, prepared during the previous step, followed by diisopropylethyl amine (2.275 mL, 12.25 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure to afford (R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid which was used for the next step without further purification.

Workup

  1. customprepared during the previous step
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-789e0bf7a4cc415cafbdf55428416b8f
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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