Cyclohexylmethane sulfonyl chloride → HCID 86755841, compound

HRID 1954076Notes

Reaction equation

HRID 1954076 reaction equation
C12CC(CC1)C([C:8](=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=1)N2.C1(CS(Cl)(=O)=O)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:24][O:23][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[O:25])[CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 3871475Cyclohexylmethane sulfonyl chlorideHCID 15479427HCID 15479427, compound

Product 1

HCID 86755841HCID 86755841, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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)).

Workup

  1. washThe reaction mixture was washed with 1N hydrochloric acid (HCl)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was chromatographed on 20 g of silica using 3:1 hexanes

Sources & evidence

ORD record
ord-e12dd49d59fa4550ba1d9e4c5dfa5727
Source dataset
uspto-grants-2000_09
Patent number
US06121280

Reaction notes

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