4'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[3,2-c]pyridine] → Spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[3,2-c]pyrdine]

HRID 48523Notes

Reaction equation

HRID 48523 reaction equation
Cl[C:2]1[C:7]2[CH2:8][C:9]3([CH:15]4[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]4)[CH2:11]3)[O:10][C:6]=2[CH:5]=[CH:4][N:3]=1>CO.[Pd]>[O:10]1[C:6]2[CH:5]=[CH:4][N:3]=[CH:2][C:7]=2[CH2:8][C:9]21[CH:15]1[CH2:14][CH2:13][N:12]([CH2:17][CH2:16]1)[CH2:11]2

Participants

4

Reactant 1

HCID 220458694'-chlorospiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[3,2-c]pyridine]

Product 1

HCID 22045857Spiro[1-azabicyclo[2.2.2]octane-3,2'(3'H)-furo[3,2-c]pyrdine]Yield 104%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[3,2-c]pyridine] (125 mg or 5.0 mmol) from Example 33 was dissolved in 50 mL of anhydrous methanol, and 25 mg of 10% palladium on carbon was added. The bottle was placed on the Parr apparatus under hydrogen atmosphere and shaken for 2.5 hours. The Pd/C was removed by filtration and washed with methanol. The solvent was removed in vacuo and the residue was taken up in chloroform and methanol and transferred to a vial. The solvent was removed in vacuo and chased with two portions of ether. After drying with high vacuum obtained 112 mg of off-white powder (104% with residual solvent.) Electrospray MS 217 [MH]+.

Workup

  1. customThe Pd/C was removed by filtration
  2. washwashed with methanol
  3. customThe solvent was removed in vacuo
  4. customThe solvent was removed in vacuo and chased with two portions of ether
  5. customAfter drying with high vacuum

Sources & evidence

ORD record
ord-361b1f9e172e44f39b5cd5daa0089fde
Source dataset
uspto-grants-2004_03
Patent number
US06703502B2

Reaction notes

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