Cyclohexylmethane sulfonyl chloride → HCID 86755841, compound

Participants

Reaction Steps

A mixture of 85 mg (0.24 mmol) of 1-(2-aza-bicyclo[2.2.1]hept-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one (mixture of exo and endo isomers), 70 mg (0.36 mmol) of cyclohexyl-methanesulfonyl chloride (J.Org.Chem. 1951; 16 621-624) and 58 mg (0.48 mmol) of 4-dimethylaminopyridine in 10 ml of methylene chloride was stirred at room temperature for 14 hours. The reaction mixture was washed with 1N hydrochloric acid (HCl), dried (Na2SO4), and evaporated. The residue was chromatographed on 20 g of silica using 3:1 hexanes:ethyl acetate as the elutant. Appropriate fractions were combined to yield 4 mg of 1-(2-cyclohexylmethanesulfonyl-2-aza-bicyclo[2.2.1]-exo-hept-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one (Rf=0.5). 1H NMR: (CDCl3) δ 6.40 (s, 2 H), 4.05 (m, 2 H), 3.80 (s, 6 H), 3.75 (s, 3 H), 2.90 (m, 2 H), 2.62 (s, 1 H), 2.50 (m, 4 H), 2.10 (m, 1 H), 1.90 (m, 4 H), 1.60 (m, 15 H), 1.20 (m, 1 H) ) and 10 mg of 1-(2-Cyclohexylmethanesulfonyl-2-aza-bicyclo[2.2.1]-endo-hept-3-yl)-5-(3,4,5-trimethoxy-phenyl)-pentan-1-one (Rf=0.4)13C NMR: (CDCl3) δ 6.40 (s, 2 H),4.50 (s, 1 H), 4.20 (s, 1 H), 3.90 (s, 6 H), 3.86 (s, 3 H),2.8-3.1 (m, 3 H), 2.5 (m, 4 H), 1.8-2.0 (m, 4 H), 1.4-1.8 (m, 15 H), 1.1 (m, 2 H)).

Provenance & Evidence