Methanol → Tert-butyl 3-(6-amino-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

HRID 914742Notes

Reaction equation

HRID 914742 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:16][CH:15]3[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]([CH2:13][CH2:14]3)[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.CO>[Pd].C(O)C>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:16][CH:15]3[N:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]([CH2:13][CH2:14]3)[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 67356030Tert-butyl 3-(6-nitro-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 67357179Tert-butyl 3-(6-amino-3-pyridinyl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 10A (200 mg) was treated with 10% Pd/C (20 mg) in a 1:1 mixture of methanol:ethanol (5 mL) under a hydrogen atmosphere (1 atm). After filtration to remove the catalyst, the filtrate was concentrated and the residue triturated with diethyl ether to afford the title compound as a violet solid.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-b10993cff3c346a5880a6165ad6e8bb0
Source dataset
uspto-grants-2007_09
Patent number
US07265115B2

Reaction notes

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