Pyridine → 5-(1-Acetoxy-3-naphthylsulfonyl)-2-thia-5-azabicyclo-[2.2.1]heptane

HRID 725789Notes

Reaction equation

HRID 725789 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[CH2:25][CH:22]([NH:23][CH2:24]1)[CH2:21][S: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:23]2[CH2:24][CH:19]3[CH2:25][CH:22]2[CH2:21][S:20]3)(=[O:17])=[O:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 166383892-Thia-5-azabicyclo[2.2.1]heptaneHCID 197087394-Acetoxy-2-naphthalenesulfonyl chloride

Product 1

HCID 197087025-(1-Acetoxy-3-naphthylsulfonyl)-2-thia-5-azabicyclo-[2.2.1]heptaneYield 35.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Acetoxy-2-naphthalenesulfonyl chloride (375 mg, 2.50 mmol) and 2-thia-5-azabicyclo[2.2.1]heptane (711 mg, 2.50 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 3% acetone in CHCl3 to provide of the pure product as a white foam (321 mg, 35% yield): 1H NMR (CDCl3) δ 1.60-1.79 (2H, m, CH2), 2.48 (3H, s, CH3CO), 2.98 (1H, dd, J=7.78, 2.44 Hz, 1/2 CH2), 3.18 (1H, d, J=10.21 Hz, 1/2 CH2), 3.51 (2H, br m, CH2), 3.67 (1H, d, J=9.48 Hz, CH), 4.70 (1H, s, CH), 7.61-7.70 (3H, m, ArH), 7.94-8.05 (m, 2H, ArH, 8.28 (s, 1H, 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-e60f9e64a74a4a54bf8d80e38672ec02
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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