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

HRID 1750228

反応式

HRID 1750228 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-7bc686e44169495298bb440529623f9f
出典データセット
uspto-grants-2015_10
特許番号
US09156796B2

関連ノート

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