Tert-butyl 8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate → Tert-butyl 8-(6-aminopyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

HRID 1431055Notes

Reaction equation

HRID 1431055 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH:11]3[CH2:17][CH2:16][CH:15]2[CH2:14][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]3)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 66743231Tert-butyl 8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66742564Tert-butyl 8-(6-aminopyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 8-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (330 mg, 987 umol) in 10 ml of Methanol was added 10% Palladium in carbon (10 mg. The reaction mixture was hydrogenated 2 hr under 50 psi hydrogen. The reaction mixture was filtered through pack of celite and concentrated to afford 300 mg (100%) of tert-butyl 8-(6-aminopyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane-3-carboxylate as colorless oil. This product was used in subsequent steps without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through pack of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-52d3894b9d1e4abaac9d56f35ec27338
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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