HCID 53708919, compound → HCID 11481657, compound

HRID 889869Notes

Reaction equation

HRID 889869 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 53708919HCID 53708919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11481657HCID 11481657, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the enantiomer (R)-(−)-5′-nitrospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine] (3.8 g, 13.3 mmol) and 10% palladium on carbon (48% water wet, 270 g) 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 pressure; the residue was purified by flash chromatography (eluting with ammoniated chloroform/methanol, 95:5 to 85:15), provided the title compound (2.5 g, 10.8 mmol, 81%): 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 under reduced pressure
  3. customthe residue was purified by flash chromatography (eluting with ammoniated chloroform/methanol, 95:5 to 85:15)

Sources & evidence

ORD record
ord-ee008c8f993445db910e34eff0bebac5
Source dataset
uspto-grants-2006_02
Patent number
US06995167B2

Reaction notes

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