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

HRID 1750228노트

반응식

HRID 1750228 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-7bc686e44169495298bb440529623f9f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156796B2

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