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

HRID 725790Notes

Reaction equation

HRID 725790 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.N1C=CC=CC=1>C(Cl)(Cl)Cl>[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 3

HCID 1049PyridineHCID 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 1

HCID 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 hr. At this time the solvent was evaporated under reduced pressure and the residue was partitioned between EtOAc and 1N aq HCl. The EtOAc was then washed with saturated aq NaHCO3, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography using 1% acetone in CHCl3 to provide the pure product as a white foam (712 mg, 63% yield): 1H NMR (CDCl3) δ 1.52-1.84 (8H, m, 4×CH2), 2.02-2.13 (2H, 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 aq HCl
  3. washThe EtOAc was then washed with saturated aq NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-df69a9f8c50a47e782d6b6285023473c
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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