Reaktion #812971

Reaktionsgleichung

4-Acetoxy-2-naphthalenesulfonyl chloride

2-thia-5-azabicyclo[2.2.1]heptane

pyridine

→

product

Ausbeute 35.3%

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

Ausbeute 35.3%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAt this time the solvent was evaporated under reduced pressure
2. 2
   Sonstigethe residue was partitioned between EtOAc and 1N aq HCl
3. 3
   WaschenThe EtOAc was then washed with saturated aq NaHCO3
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash chromatography

Vorschrift

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).

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