7-Azabicyclo[4.1.0]heptane, 7-[(4-methylphenyl)sulfonyl]- → 4-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamide

HRID 1750228Notes

Reaction equation

HRID 1750228 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:16]3[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]3)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:18][Li]>C1COCC1.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[CH3:17][C:1]1[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@@H:16]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[CH3:18])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 118318857-Azabicyclo[4.1.0]heptane, 7-[(4-methylphenyl)sulfonyl]-HCID 178418348HCID 178418348, compound

Product 1

HCID 155078474-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamideYield 62%

Reagents, catalysts & solvents 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 180 g of) 7-(Toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane and 18 g of Copper(II)acetyl acetonate in 1500 ml of dry THF was added 86 ml of a 10 M solution of methyllithium dropwise over 30 min. The mixture was stirred under nitrogen atmosphere for 8 h. It was then washed with water and extracted with ethyl acetate twice. The combined organic layers were concentrated. The resulting residue was purified by chromatography (silica, hexan/ethyl acetate) to afford 120 g (62%) of 4-Methyl-N-(trans-2-methyl-cyclohexyl)-benzenesulfonamide

Workup

  1. washIt was then washed with water
  2. extractionextracted with ethyl acetate twice
  3. concentrationThe combined organic layers were concentrated
  4. customThe resulting residue was purified by chromatography (silica, hexan/ethyl acetate)

Sources & evidence

ORD record
ord-7bc686e44169495298bb440529623f9f
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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