3-Azabicyclo[3.2.2]nonane → 3-(1-Acetoxy-3-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonane

HRID 725781Notes

Reaction equation

HRID 725781 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([S:15](Cl)(=[O:17])=[O:16])[CH:6]=1)(=[O:3])[CH3:2].[CH:19]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[CH2:22][NH:21][CH2:20]2>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([S:15]([N:21]2[CH2:22][CH:23]3[CH2:26][CH2:27][CH:19]([CH2:25][CH2:24]3)[CH2:20]2)(=[O:17])=[O:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 92403-Azabicyclo[3.2.2]nonaneHCID 197087394-Acetoxy-2-naphthalenesulfonyl chloride

Product 1

HCID 197087163-(1-Acetoxy-3-naphthylsulfonyl)-3-azabicyclo[3.2.2]nonaneYield 63.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

4-Acetoxy-2-naphthalenesulfonyl chloride (861 mg, 3.02 mmol) and 3-azabicyclo[3.2.2]nonane (379 mg, 3.02 mmol) were combined in CHCl3 (20 ml) and pyridine (20 ml), and the mixture was stirred at room temperature for 15 hours. At this time, the solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc and 1N aqueous HCl. The EtOAc was then washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography using 1% acetone in CHCl3 to provide 712 mg of the pure white product as a white foam: 1H NMR (CDCl3) δ 1.52-1.84 (9H, m, 4×CH2), 2.02-2.13 (2.H, br s, 2×CH) 2.46 (3H, s, CH3CO), 3.31 (4H, d, J=4.2 Hz, 2×CH2), 7.56-7.71 (3H, m, ArH), 7.92-8.02 (2H, m ArH).

Workup

  1. customAt this time, the solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc and 1N aqueous HCl
  3. washThe EtOAc was then washed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-743bafbde43b4c94a202f2de4fccf956
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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