5'-Nitrospiro[1-azabicyclo [2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine] → spiro[1-azabicyclo[2.2.2]octane-3,2'-3H-furo[2,3-b]pyridine]-5'-amine

HRID 841067Notes

Reaction equation

HRID 841067 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH2:12][C:11]3([CH:17]4[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]4)[CH2:13]3)[O:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[CH2:12][C:11]3([CH:17]4[CH2:16][CH2:15][N:14]([CH2:19][CH2:18]4)[CH2:13]3)[O:10][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 104004255'-Nitrospiro[1-azabicyclo [2.2.2]octane-3,2'(3'H)-furo[2,3-b]pyridine]HCID 178418361HCID 178418361, compound

Product 1

HCID 15908236spiro[1-azabicyclo[2.2.2]octane-3,2'-3H-furo[2,3-b]pyridine]-5'-amineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5′-nitrospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (1.4 g 5.36 mmol), and 10% palladium on carbon (48% water wet, 270 mg) in methanol (90 mL) was hydrogenated for 1 hour at 50 psi of hydrogen. The catalyst was filtered off through a pad of celite and the solvent was evaporated under reduced to obtain the amine (1.2 g, 5.25 mmol, 98%) as a tan solid: electrospray MS (m/z, relative intensity) 232 ([MH]+, 100).

Workup

  1. filtrationThe catalyst was filtered off through a pad of celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-85bc02832fe44d7bb610a649e84d60c0
Source dataset
uspto-grants-2002_04
Patent number
US06369224B1

Reaction notes

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